


The Lucky Pairs of Christmas Underwear

by thefandomsinhalor



Category: Supernatural
Genre: Advent Calendar, Alcohol, Alternate Universe - Modern Setting, Baker Gabriel (Supernatural), Bakery, Christmas, Christmas Movies, Christmas Music, Christmas Shopping, Co-workers, Cute Gabriel/Sam Winchester, Dean Winchester Has a Crush on Castiel, Dean Winchester Needs to Use Actual Words, Financial Issues, Fluff, Gift Wrapping Booth, Holidays, Lawyer Sam Winchester, M/M, Mechanic Dean Winchester, Mutual Pining, One Night Stands, Pining, Secrets, Slow Burn, Sort Of, Supportive Winchesters (Supernatural), Underwear
Language: English
Status: Completed
Published: 2019-12-01
Updated: 2019-12-26
Packaged: 2021-02-26 02:15:29
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 25
Words: 53,802
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21635722
Author URL: https://archiveofourown.org/users/thefandomsinhalor/pseuds/thefandomsinhalor
Summary: Due to heavy workloads and conflicting schedules, Sam and Dean, living in different cities, are both disappointed when it appears that they won't be able to spend the holidays together—something they had always managed to do in the past.This turn of events, however, offers them both the opportunity to seek someone else to share their respective holidays with, and when Dean's last year crush is paired up with him at the Gift Wrapping booth, and Sam keeps running into a charming new acquaintance, by helping each other, the brothers feel hopeful that Christmas time might not be ruined after all.
Relationships: Castiel/Dean Winchester, Gabriel/Sam Winchester
Comments: 253
Kudos: 183





	1. Chapter One: A Holly Jolly Time

“Dean? Hello? Did you—are you still there?”

Sitting on a very uncomfortable chair at an overpriced café, for someone of his limited means anyway, Dean swallowed hard. Still holding the phone to his ear, he lowered his eyes as he felt his heart growing heavy at the news he had just heard.

“Dean?” repeated Sam at the other end of the line.

“Yeah. Still here. Sorry. Just—I didn’t expect that.”

“I know. I’m sorry. I feel awful. It’s just—work is crazy.”

“It’s okay, Sammy. I get it. Hell, I’m in the same situation. If not worse.”

“And this is why I’m really sorry. I had agreed to be the one to—”

“Sam, stop.” He cleared his throat. “I—it sucks, but like I said, I get it. We’ve been lucky so far, but I guess that this year…” he let out a deep sigh. He couldn’t even finish the sentence.

“I promise I’ll do my best to change it, but right now, um, it doesn’t seem like I’ll be able to join you for Christmas,” Sam said in a desolate voice.

Dean nodded blankly. “Any other good news?”

Sam let out a deep sigh in turn.

“I—I just, Dean, I hate the idea that you’ll be alone for Christmas.”

“Me? I’ll be fine, Sam. What about you? What are you going to do?”

“I’ll be okay too. I’ll be at work.”

Dean lowered his phone and shook his head for a moment, and then he brought his phone back to his ear. “That’s what I mean, Sam. You, not being able to make it here because of work, deadlines and travelling schedule, that’s one thing. But to actually work _on_ Christmas? I mean, I’m not even doing that and all I do is work.”

“I don’t have a choice. And honestly, it’s just, you know, _one day_. For a few hours. Which is really annoying when said like this, but...Work will be a nice distraction. And we can still talk. And skype for the rest of the day if you want. It’s ridiculous, but we can do it. I was almost going to suggest that we postpone Christmas and meet up soon after, but….”

“Nah. I mean, even if I knew for a fact that we could do something in the following week, I feel like we would have missed it. It would still be cool, but you know.”

“That’s what I thought too,” agreed Sam. “But we should do something for New Year’s Eve. I’m definitely working on that.”

“All right. Work will still be nuts on my end, but it should have diminished a bit by then. Or maybe I could make it to your end this time.”

“Dean, no. I—unless you let me help you out with money—”

“No,” blurted out Dean.

“—but I know you won’t agree to it,” said Sam, sighing.

Biting his bottom lip, Dean pondered on Sam’s suggestion. “I’m not saying yes, but I’ll think about it,” he brought himself to say.

“You will?”

“Just because I haven’t seen your freaking face for far too long now. But still. Not a definite yes.”

“But you’ll consider it?”

“Yeah. But it’s still too early in the month to have a clue of what the situation’s going to be at that point. So, I’ll leave it to that for now.”

“All right. That’s great,” said Sam.

Dean could hear how happy Sam was at the idea, so he decided that he should make an effort to make it happen.

“And Dean, even if for whatever reason that doesn’t work out either, I promise I’ll visit you soon, okay?”

“All right, Sammy. But don’t worry. I’m—it’s disappointing, but I know you tried. It will be okay.”

“Thanks Dean. I—thanks for understanding.” There was a long pause, and then Sam asked, “So, besides that? Anything new?”

Welcoming the change to a less depressing topic, Dean said, “Not really.”

“What about work? Is the holiday frenzy rising?”

 _A_ slightly _less depressing topic._

“The frenzy is settling in, all right,” he sighed.

“Is the music driving you nuts already?”

“It’s been driving me nuts for the last two weeks. I was actually freaking humming _Rudolph, the Red Nose Reindeer_ yesterday and I didn’t even notice it. I only did when a customer mentioned it.”

Sam let out a laugh. “Sorry. A few more weeks and it will be all over. And it’s better than last year, right? Since you’re at the _Chocolaterie_ this time. I thought you said it was a bit more shielded than the rest of the store now that they moved its location this year.”

“Yeah, well that was the plan, but not anymore.” Dean leaned back into his seat.

“What? I—what do you mean?”

“I was about to tell you earlier. I was transferred a couple days ago to another department. Sort of.”

“No! What? But why?”

Dean cleared his throat. “It just needed to be done.”

“Why? Dean, what does that mean?” asked Sam, nearly aggravated as though he already knew the answer.

Dean debated for a moment whether or not he should share the specifics with his brother, knowing that Sam would most undoubtedly be worried and annoyed at him.

Nor would he be shy to express his views about it.

And Dean had worked really hard to avoid this particular lecture.

But since Sam had been honest about his work situation, he concluded that he owed him the same courtesy.

So, Dean replied, “Because another position opened up at the last minute and it offered more hours. I gave my name and here we are.”

“Dean,” groaned Sam.

_I knew I shouldn’t have said anything._

“It’s all right, Sam.”

“Is it? How many hours are we talking about now?”

Silence.

“Dean?”

“Twenty hours.”

Sam swore loudly. “On top of your full time job at the garage? And the gig that Jo got you with Pam?”

“I was hoping you forgot about that…”

“I didn’t. Dean, this is nuts. How are you even able to pull this off?”

Dean crossed one arm over his chest, lowering his eyes.

“Bobby is helping me out. I’m solid during the day at the garage throughout the week, so I can have my nights and the weekends to do the rest.”

“That’s not what I meant. Do you even have a day off? A night off?”

“You’re one to talk, Sam. And it’s just for December. Everything will be back to normal after that.”

“December starts tomorrow and it’s already insane. And answer the question.”

Dean sighed. “I work at the store on Wednesday, Thursday and Friday nights. And in the afternoon during the weekend. And then Saturday nights, I wait at Pam’s events, which is really not a big deal. I did it this summer. It’s good money.”

“You did it once, Dean. One wedding. Not four in a row on top of—”

“No weddings this time. Pam said it will be Christmas parties for companies. The first one is tonight. It’s gonna be fine.”

“That leaves you with what, though? For free time?”

“I still have my evenings Sunday through Tuesday.”

“If you’re not pulling extra hours at the garage, you mean? Which I’m guessing you’re already doing in the mornings during the weekends? Am I right?”

“Sam,” warned Dean.

Sam remained silent for a good minute, until he said, “Dean, I’m worried.”

“Don’t be. It’s all going to go in the piggy bank so I’ll be able to catch my breath during the harsh winter,” he joked.

Sam let out a deep sigh. “And what about the new position at the store? Shit, Dean. I—I know you were really happy about—you were actually looking forward to the _Chocolaterie_. Now, I feel even worse about not being able to go.”

“It’s not your fault. And anyway, it’s just a job for the holidays. No matter what it is, we both know the novelty would have worn off eventually.”

“Okay, hold on here. Because we both know the _real_ reason you wanted to work in that department. And it had absolutely _nothing_ to do with the job in question…”

Dean pursed his lips, lifting his head to look at the ceiling, annoyed.

“Ugh. Not this again, Sam. I told you, it was…it’s not important.”

“Bull. You’ve been whining about this guy for, like, literally a freaking year now. A year.”

“Well, whatever,” urged Dean. “Doesn’t change anything now as he’s not even here.”

“But you said that last year he hadn’t shown up until a week or so before Christmas.”

“I said I only _noticed_ him at the end of the season. Nuance.”

“But you also said they had added employees as Christmas approached. So maybe he was one of them. And he will be this year too.”

Dean let out a sigh. “I don’t know, Sam. All I can do is wait and see.” And after a short pause, he added in an urgent manner, “If I cared. Which, I don’t. Not really.”

Sam snorted. “Right.”

“What about you, huh? Made any headway with _your_ office crush?”

“I—there’s been progress.”

“Yeah? Asked her out yet?”

“In a manner of speaking.”

At the sound of Sam clearing his throat, Dean shook his head.

“Did you or did you not ask her out, Sam?”

“I…okay, I haven’t yet, but—”

“God, Sam,” said Dean, cutting him off. “What are you waiting for?”

“If you would let me finish, I was going to say I’m going to. I’m just waiting for the right opportunity.”

“And when’s that? On your wedding day?”

Sam huffed. “I’ll get to it. The timing and the setting have to be right.”

Dean was not impressed by this statement.

“Don’t wait too long.”

“I won’t.”

Not wanting to push it too far, Dean asked, “Got anything else planned for today?

“Not sure. Kevin texted me. He and some of his friends are going out tonight. He told me the address of the bar. He said he invited Bela too…”

“Perfect! You can make your move then. You’re going, right?”

“I don’t know. I have so much work to do.”

“Sam, I swear if you don’t go, I will somehow teleport to Chicago and drag you there myself.”

“Dean, this isn’t really my scene.”

“That’s precisely why you should go. Live a little. And if Bela’s there, she gets to see you somewhere else than at the office. A different setting, like you’ve been waiting for. And if she’s not there, you still get to have fun.”

“But hitting on her at a bar? Like, that’s just—that’s not really how I had pictured it.”

“Sam, maybe start by finding out if she’s interested? And when you know that she is, feel free to execute whatever fantasy of courtship you had planned out,” he said with a grin on his face. “At least, go to the damn bar and enjoy yourself, huh?”

“In which department are you working at _The_ _Milton’s_ now?” asked Sam.

“Changing the subject, huh? Nice try.”

“I’ll think about what you said,” he assured him. “But I’m curious and you didn’t say earlier.”

_There was a reason for that._

“The…I’m working at the Gift Wrapping Booth.”

There was a pregnant pause. “Sorry, the what?”

Dean groaned. “You heard me.”

After a long pause, Sam said, “I see.” Sam hadn’t laughed, but Dean knew full well his brother was most likely holding down a massive fit of laughter. “I’m—wait, aren’t those usually managed by volunteers? And it’s for donations or—”

“It still is. The donation part, I mean. Look, I don’t know the whole story, but apparently there was an issue last year with some of the volunteers, so this time, they decided to offer their own Gift Wrapping services. Nothing has changed. Every customer is entitled to the services, to donate however much they want, and all the funds goes to the Children’s Hospital, just like last year. The only difference is that the store is employing people instead of relying on volunteers.”

“Is this unusual?”

“I have no clue, but it creates jobs, so I’m not gonna complain about it. It’s actually kinda nice of them to do that since they really don’t have to. And the store is providing the wrapping paper and everything, and let me tell you, it’s not the cheap stuff either.”

“Cool. Cool. I just have one question.”

Dean rolled his eyes. “Oh, yeah? What’s that?”

“Had they seen you wrap anything before they gave you the job or…”

“It’s wrapping, not rocket science.”

“Dean.”

“I’m fine,” he said defensively. And then, after a short hesitation, he added, “They do have a certain fancy way of doing it.”

“Thought so.”

“But I’ll manage. I practiced at home a bit—I mean it’s wrapping for God’s sake!”

“I’m sure you’ll do just fine, Dean. I was just curious,” said Sam sincerely. “And how do you feel about it so far?”

“Well,” sighed Dean, “honestly, it’s been somewhat uneventful. I’m the only one in the booth—it’s more like a box, but whatever. At least I don’t have anyone boring to tear my ears off, but people haven’t been super eager to have their purchases wrapped so far. So it’s basically been me, sitting on a stupid chair and looking at people buying stuff I can’t afford. While listening to the same twelve songs.”

“Well, I don’t know if that’s encouraging or not, but I’m pretty sure the pace will pick up soon enough.”

“Yeah. Not sure that’s a silver lining.” Moving the phone away from his ear, Dean looked at the time on his phone. “All right,” he said, after putting the phone back, “I have to head back. My break is almost over. I’m lucky they even give me one, so… Thanks for the phone call.”

“Same. Though, I wish I had better news. Hang in there, Dean. The holiday season will be over soon.”

“I will. I’ll call you back tonight after my gig. And you better not answer because you’re out having fun for once,” he said with glee.

“We’ll see.”

“You freaking better.”

“Fine! Bye!”

Dean, walking to his booth, trying not to drag his feet, passed by toys’ department and spotted his friends, Charlie and Jo, looking at the board games.

Not in a talking mood, he simply waved at them and continued his route.

“Dean, wait!” said Jo.

Dean came to halt and let his friends catch up to him. “Sorry, I have to go back.”

“We’ll walk with you a minute,” said Jo. “Are you still good for tonight?”

“Yup. Pam called me Thursday night to double check. She gave me the address and everything. And a reminder of the regulations. I’m trying not to take it personally,” he said, beaming.

“Don’t. She did the same for me too.”

“Thanks again for giving her my name.”

“No problem.”

“You going too, Charlie?”

“Yes,” she sighed. “Which sucks. That’s when I had my D&D meet ups.”

“Create a new one, then,” said Jo. “I’ll join.”

Charlie lifted an eyebrow. “Don’t toy with me, Harvelle.”

“I wouldn’t dare.”

Then Charlie, smiling, said, “You think we can convince this one, too,” she said, poking Dean’s chest with her finger.

“If I had time to have a life,” he said, “I would.”

Charlie squinted at him. “We’ll have to see about that then.” Continuing walking side by side, she asked him, “So, do you like your new position, Dean?”

“I’m not thrilled, but it’s not bad, either. And if I’m honest, it’s certainly an improvement from last year…”

“That wasn’t very hard to beat,” pointed out Charlie, remembering full well as she had been stuck in the same boat as he had.

“True.”

Having reached the booth, Dean pushed the half-door, stepped inside the booth, and approached the counter facing the girls.

“Wait, I thought you were at the _Chocolaterie_?” said Jo. “That was like perfect for you.”

“Yeah. I agree,” said Dean. “But I switched for the hours.”

“So, who is manning the _Chocolaterie_ now?”

“Meg,” said Charlie. “I saw her this morning.”

“What?” exclaimed Dean. “Oh, man! I didn’t even know she was back.” And he made a face of disgust.

“She’s actually not that bad,” said Charlie.

An opinion that was not, it seemed, overly shared with her friends.

“Not that I care about that kind of stuff, but she always seemed kind of a manipulator to me,” said Jo.

“I don’t trust her,” said Dean simply.

Charlie lifted an eyebrow. “Um, one, you barely trust anyone. And two, I’m pretty sure the main reason why you don’t like her is because you saw her lurking around that guy you had heart-eyes for last year.”

Jo turned briskly towards her. “What’s that now?” A smirk appeared on her face. “What guy?”

“You didn’t know this?” asked Charlie.

“No. What guy?” she repeated.

“No one,” said Dean, busying himself by moving the wrapping paper around, which was utterly unnecessary.

“ _Not_ no one,” said Charlie. “Last year, there was this guy—dark hair, killer blue eyes, about yay-high—he was one of those last-minute employees. You know the ones who are brought in within the last few days before Christmas for emergencies, substitution or additional help?”

Jo nodded, understanding and eager to hear the rest.

“Okay, well, last year,” she continued, “Dean and I were elves helping out kids to have their picture taken with Santa. Which was not very far from the _Chocolaterie_. And this guy showed up just a few days before Christmas for additional help there, and from that moment on, all Dean did was constantly stare at his pretty face.”

“I didn’t _constantly_ stare at him…”

“You didn’t ask him out?” said Jo.

Dean, pursing his lips, let out a deep sigh. “I never got to. As it was the last days before Christmas, I didn’t have one second to myself. I don’t even know his name or even exchanged a few words with him. And I didn’t work here after Christmas. I, um, did stop by the store a few times, but…and since I’ve been back, I tried to find out if anyone knew anything, but I haven’t had much luck so far.”

“I asked around too since they kept me on after Christmas, but nothing,” said Charlie.

“The only one who may have something is Meg and the only thing she had said to me last year was that his name was Clarence and I’m pretty sure it’s a goddamn lie. Hence: I don’t trust her.”

“Uh-huh. Were they a thing?” asked Jo to Charlie. “‘Clarence’ and Meg, I mean.”

“Who knows?” said Charlie. “It’s possible. I think Meg was the only one who got to interact with him. But he didn’t stay around for that long and I haven’t heard anything suggesting that either. The guy’s a mystery.”

Frowning, something was still bothering Jo. “Why not ask Rowena? If anyone knows who he is, it would be her, no?”

But Dean and Charlie shook their heads. “Rowena wasn’t here last year, remember? It was that atrocious-ass Adler.”

“Right. I think I had repressed that,” she said with a grim face. “Still, there has to be a way to find out. A record or something?”

But Dean was officially done with the subject. “Whatever,” he shrugged. “It’s not like my life depends on it. It was, like, one guy. Who may or may not have been good-looking. From afar. Whatever.”

Charlie and Jo exchanged devious looks.

Ones that made Dean roll his eyes. He waved them goodbye, as he knew they both needed to head back to their own departments, and watched them stroll down the aisle.

And so, left by himself, and with no customers in sight (for him, at the very least), just as he had told Sam, Dean pulled up a chair, sat down and…waited.

Attempting to seem alert and ready to help.

And not appear overly depressed at doing nothing.

_At least it’s not complicated and it certainly beats dealing with rude customers._

On the other hand, killing time by staring in front of him blankly felt like a waste of time. Even if he was technically earning money while doing it.

But he knew he shouldn’t complain. As Sam had mentioned earlier, soon enough, he would most likely reminisce on the time when he was bored out of his skull.

But being kept in that booth with nothing else to do but to watch the people around him, while he was stuck alone, served as a painful allegory to his life. Everything around him was moving and there he stood, waiting for someone to come to him, while he was expected to just smile as if he was having the time of his life.

And now, the one silver lining he had had for the holidays was apparently gone as well.

No Sammy. No traditional cookies. And no making fun of old Christmas movies, while eating junk food and drinking eggnog.

They had never spent Christmas apart before. Even when Sam had been away at college. Even when either of them had been in a serious relationship (though that had mostly been Sam’s case, not Dean’s), they had still celebrated the holidays together.

No matter what. That was their thing.

And now he would have to spend it on his own.

Alone.

Assuming he would survive the crazy amount of workload awaiting him in December.

And not be driven mad by this infuriating Christmas music.

_Awesome._

_I hate my life._

“Hello.”

Dean nearly jumped out of his skin. A hand over his heart, he turned to his left only to realize someone was standing next to him.

In the booth.

“My apologies, I didn’t mean to startle you. I was told to join you today.”

Regaining his composure, Dean said, “Cool. Um, the place has been pretty de—”

And the rest of his sentence died in his throat, the moment his eyes fell on his new co-worker.

Dark hair.

Killer blue eyes.

About yay-high.

_It’s him._

_And he’s here._

_With me._

_At the freaking booth._

Dean gawked at him.

_Chapped lips._

_Stubble beard._

_And a deep voice that—_

_And all I’ve been doing is staring at him like a complete moron._

“Hi!” Dean nearly yelled, waving his hand.

_Stop now._

And he immediately dropped his hand.

“Hello,” the man repeated.

“Dean,” said Dean, pointing at himself.

“Hello, Dean. I’m Castiel. Nice to meet you.”

_Castiel._

“Um, same. Hi, Castiel.”

And he smiled at him like an idiot.


	2. Chapter Two: The Gift Wrapping Booth

It took Dean a long time to realize that he had been helplessly gawking at his new co-worker.

For far too long.

Embarrassingly long.

“Dean?”

“So, this is the wrapping booth,” said Dean urgently, after finally snapping out of it.

“Yes, I gathered as much,” said Castiel, chuckling.

_Jesus. Get a grip._

“Right, sorry. Did you go through the basics with Rowena?”

Castiel nodded. “And she told me you’d explain the rest about the booth, though I’m fairly certain it’s rather self-explanatory.”

Dean let out a laugh. “You’re right about that.”

He cleared his throat, and then quickly showed Castiel where the equipment was, which took less than a minute.

“You can use standard wrapping methods, obviously, though the store would like to be a little more creative. They offered a few patterns that you can follow here.” Dean retrieved the thin file he had been handed on his first day. It contained a multitude of schemas of different wrapping methods. He had since practiced a few of them when he had been bored.

But perhaps not as extensively as he should have.

“Do we have to do these ones exactly?” asked Castiel, skimming through the document.

“No. It’s just a suggestion. You can be even more creative too. But not too…”

“Bold?”

“Yeah. The booth still represents the store and well,” Dean made a face, glancing around.

Castiel sighed and stopped on one page, examining it more closely.

“Fascinating, huh?” joked Dean.

Turning his focus on Dean, Castiel said, seemingly amused, “Am I to understand that working at the booth wasn’t your first choice?”

“Not really, no. It’s better than what I had last year. Although, I feel like it comes to the same eventually when you have this music playing over your head.”

“You may have a point, there,” said Castiel, smirking. “What would have been your first choice then?”

“I don’t know.” Dean hesitated a moment, and then added, with caution, “The, um, _Chocolaterie_ would be pretty cool.”

Castiel nodded. “I have to admit that is a good one. I worked there last year, though very briefly, and it actually smells delicious.”

“I know.”

Castiel frowned. “What?”

“I mean,” blurted out Dean, panicking, “I got to work there for like a week before I switched here.”

“Oh.” Castiel was observing Dean in a manner that made him unsure how his new co-worker felt.

Feeling he needed to elaborate, Dean said, “More hours this way.”

Castiel nodded.

After glancing around and assessing that no customer was anywhere near them, Dean gestured for Castiel to take a seat so they would be more comfortable.

“So, did you say you worked here as well? Last year, I mean?” asked Castiel.

Dean nodded.

_God. Don’t ask me where._

“Which department?”

_Shit._

Dean actually considered lying. But because most people who were employed for the holiday season at _The_ _Milton’s_ were returning employees from the previous year, like him and Castiel, he reasoned that, sooner or later, someone would most likely mention it.

And then he would have to explain something far worse than a stupid elf outfit: he would have to explain why he had lied.

 _Though, I’m pretty sure anyone on this earth would understand why I’d lie about_ that.

He took a deep breath and said, “Promise you won’t laugh?”

Castiel frowned at Dean’s comment, but he nodded.

“I was one of Santa’s elves.”

Castiel opened his mouth for a second, as though he was about to say something, but no sound came out, and then he shut it again.

He was not laughing, or even holding down laughter or a grin, as Dean had expected.

But he was staring at him in an odd fashion.

Just as Dean was about to ask him if something was wrong, Castiel said, “That wasn’t too far from where I was last year. They changed its location this year but—” He stopped for a second. “It’s unfortunate I was only there during the last week. It was so busy. I didn’t have the chance to meet much of anyone.”

“Yeah, well, you’re here now,” said Dean, lowering his eyes, desperate to not expose himself.

“That’s very true.”

And by the way Castiel was scanning his face, Dean had the impression that he had failed in this task.

“So, um, Dean? I’m curious.” Castiel shifted on his seat, changing his whole body position. Dean, now officially worried, braced himself for Castiel to reveal that he had known all along about Dean’s massive crush on him.

But that was not what Castiel asked him.

“As this is a holiday gig,” said Castiel, “I’m guessing you occupy your time otherwise?”

Dean exhaled in relief. “Um, yes. I’m—I’m actually a mechanic.”

“How interesting. That’s such a useful trade,” he said.

“It is.” He nearly expected Castiel to inquire as to why he was working at _The Milton’s_ , but Castiel remained silent.

And Dean had been grateful that Castiel hadn’t pried too much on why he necessitated a second job.

_Or a third one._

_Which I’m certainly not going to mention._

_Not that there is anything wrong with that._

After all, Dean concluded that Castiel, by being stationed at the same booth that he was for the holidays, probably shared a similar financial situation to his own.

“And what about you? What do you do when you’re not wrapping presents?” he asked him.

“Oh, I—I don’t exactly have a specific trade like you,” said Castiel. “I—I bounce from one thing to the next, I’m afraid. The main thing that I do right now is,” and then he paused, letting out a sigh. “I’m tutoring. Not anything excessive. I’m, um, actually looking for something else.”

Given his last comment and how serious his expression had suddenly turned, Dean sensed that there had been a ‘but’ at the end of his sentence.

As if he had been reading Dean’s mind, Castiel said, “Sorry. That might have sounded a little more negative than I had intended.” He smiled shyly, crossing his arms over his chest.

“Don’t worry. I get it. You’re just trying to find something that’s…more you?” he suggested.

And Castiel nodded, biting his lips.

“I was lucky,” said Dean. “I always loved cars. And my boss is basically family. It wasn’t complicated. And I might not exactly be rolling in gold by being a mechanic, but I love it. And I can’t really see myself doing anything else. You’ll get there.”

Fearing that he might have given Castiel the perfect opportunity to question him about his presence at _The Milton’s_ , especially considering how slightly patronizing his last comment might have sounded, Dean braced himself for an inquiry.

But once again, if Castiel had questions, he kept them to himself.

He smiled warmly at him and said, “Thank you. For saying that.”

They observed one another for a moment, and when Dean was beginning to feel the blood rushing to his cheeks under Castiel’s kind eyes, he said, “So, um, Cas, how—can I call you Cas?”

Castiel nodded.

“How long have you—” Dean had begun saying, but he stopped mid-sentence when he was suddenly interrupted.

“Well, well, well. Look who’s back?”

Someone was standing in front of the booth.

“Long time, no see, Clarence.”

_Ah, fuck no. Go away._

“Hello, Meg.”

“Hi,” she said in faint voice, smirking in a way that rendered Dean simultaneously annoyed and uncomfortable.

_Damn it. This was actually going well._

_I think._

“What are you doing here?” she asked Castiel.

He frowned at her. “Working?” he suggested, unsure.

“I mean here,” she said, tapping on the counter. “The _Chocolaterie_ is that way.” She nodded her head to her right, expecting Castiel to follow her.

“I’m not working there this year.”

She lifted an eyebrow. “Did you ask for this?”

“The Wrapping Booth? I expressed my interest, but I’m not above the rules. Like everyone else, I gave my name and I went where management sent me.”

“I see.”

“It’s a happy accident.”

“Is it?”

Castiel nodded. And then everyone remained silent for a good minute, during which Castiel and Meg appeared to be undertaking their own conversation simply by exchanging looks.

Finally, smiling, Castiel said, “Was there anything else?”

“Just wanted to say hi. For now.”

“Well, hello.”

Castiel’s tone hadn’t been degrading or rude. Not even sarcastic. He didn’t appear to hold any rancor against her. But the way Meg’s entire attitude had changed in a split second had made Dean conclude that something was amiss.

“We’ll catch up later, I suppose.”

“I guess we will,” she said, holding her stare on him. She then shifted her eyes on Dean, giving him a stern look as if she was personally holding him responsible for whatever she was annoyed with in that moment, only to then turn on her heels and disappear down the aisle.

Castiel repositioned himself on his seat to look at Dean properly again, and said, “What was I saying before? Or was it you who was speaking?”

“I—um, I don’t really remember.”

“Oh, well. It will come back to us. So, tell me Dean, care if I try one of these wrapping patterns? And maybe we can trade the funniest stories we have about the customers of this place from last year? I’m sure yours must be interesting given the job in question.”

Dean smiled at him. “Deal.”

And Dean enjoyed the rest of his afternoon with Castiel. Though their conversation didn’t exceed more than this in term of content, Dean had to admit that his mood had drastically changed for the better by the end of his shift.

And this, in ways he certainly hadn’t predicted. And now he couldn’t wait to tell Sam.

And with that turn of events, Dean, hoping his brother would catch a break for once, wondered if Sam would listen to him and meet up with his friend at the bar later that night.

Little did he know that not only would Sam indeed follow his advice, but Sam would have, in fact, quite an eventful night as well.

Just not in the way either of them could have predicted.

**Notes for the Chapter:**

> Thank you for reading! I hope you enjoyed it :)  
> And a big thank you to Danica and Landrala!!
> 
> Have a nice day!!


	3. Chapter Three: A Night Out

Sam had been incredibly depressed at the idea of spending the holidays without Dean.

And, not to mention, on his own.

Even if they never did anything grand, due to a lack of funds or a tight schedule, they nonetheless always managed to have a bit of fun. And considering how depressing the holidays often were for so many people, the fact that he and Dean had, somehow, always managed to have a good time had been something Sam had prided himself on.

But this year would be different, it seemed.

Throughout the month of November, assessing that his workload was constantly increasing with no signs of slowing down, despite the fact that the holidays were right around the corner, Sam had grown worried they wouldn’t be as lucky this time.

And yet, he had remained hopeful that a miracle would manifest itself into thin air, and make everything right for them. So, he had delayed informing Dean of that grim possibility, thinking of saving his brother from an unnecessary worry.

On that Saturday morning, however, when he, alongside many of his co-workers, had been assigned to a new case—one that his boss, Miss Knight, had implied was an “all hands on deck” situation—Sam understood that no alternative would present itself for them this year.

After sharing the sad news to Dean, Sam felt blue for the rest of his day. So much so, that by evening’s time, even with his daunting workload that needed urgent tending, Sam grew tired and frustrated at looking at all his papers scattered over his kitchen table and decided to follow Dean’s advice.

He changed his shirt, washed his face quickly, texted Kevin, and the next thing he knew, he found himself stepping into the pub.

Yes, pub, not _club_ , as Kevin had implied in his latest text to Sam once he had informed him he would join him after all.

It wouldn’t have been a problem, save for the fact that the place was screaming health codes violations.

The lighting was practically non-existent, the customers gave him a weird vibe, and Sam didn’t dare look at the floor, considering how sticky it was.

Uncommonly so, even in bar standards.

And that was for starters.

_Kevin, how the hell do you find these dumps?_

Making his way across the room, he soon spotted Kevin waving his hand at him, catching his attention. He reached the booth, where he recognized familiar faces, some from Kevin’s circle of friends and others from their work.

Including, unfortunately, Becky Rosen.

Who was undeniably cheerful to see Sam had joined their evening.

And wasn’t too shy to express it.

Not even a little.

Sam, taking a seat next to Kevin, waved awkwardly at her, and then, as subtly as he could, he shot an angry look at Kevin, who was holding down a grin. Once he noticed that Becky was busy speaking to Harper, another of their co-workers, Sam told Kevin, “You could have told me she was here.”

“But then you would have chickened out and stayed home.”

“Maybe. Maybe not. But at least I would have mentally prepared myself for an entire evening of me turning her down.”

“Come on, Sam. She’s not that bad.”

Sam made a face.

“Maybe I should warn you that Kip is also here,” said Kevin. “And we all know he likes you too.”

Sam groaned. “I’m leaving,” he said, sliding himself to the end of the booth. But Kevin stopped him.

“Don’t leave. You just got here. Stay an hour at least? Channing is not even here yet and she’s dying to meet you.”

Sam sighed, shaking his head. “Fine. I’ll stay. _For Channing_. Who clearly needs to come to her senses to follow you to a place like this…how—what is this place?”

“An old, um, acquaintance of mine knew about it. Everything is cheap. It’s perfect for a night out.”

“To what? Catch your death?”

Kevin let out a laugh. “You’ll be fine. _Billie’s_ is great.”

Sam remained unconvinced as he scanned the surroundings. But soon enough, after having sipped on a beer and laughed with Kevin and the others occupying the booth, Sam had to admit that he was having a good time.

And, just as Kevin had said, even Becky had been excellent company and on her best behavior—despite the flagrant heart-eyes she had been giving him, but Sam figured that these might not dissipate anytime soon.

Still, her attitude hadn’t been as bad as he had initially feared.

Channing eventually showed up and Sam was very pleased to finally meet Kevin’s girlfriend whom he always spoke highly of.

While he was enjoying himself, listening to everyone’s crazy stories and random ramblings, Sam had also been glancing around the room in the hope of spotting Bela.

But she had been a no-show.

His luck changed, however, in the second hour when Sam was on his third beer, trying to pace himself.

Or so it seemed.

Bela was standing at the bar talking to the bartender, her phone in hand.

Sam immediately turned towards Kevin, half-panicking.

“She’s here.”

“I know. I invited her. You’re welcome,” said Kevin, taking a sip of his beer.

Sam glanced at her again, but remained on his spot.

“I can’t believe _I’m_ the one who has to explain this to _you_ , but this is the part where you walk up to her. And talk,” his friend told him, nudging him on his shoulder.

Sam nodded. He left the booth, took a deep breath, fixed his hair and walked straight ahead.

Finally.

A place outside of work, where he could have a shot.

Although, a skeevy-looking bar, where he could barely hear himself think, wasn’t that much of an improvement, he thought.

But at least, the fact that it would occur outside billable hours made him feel better.

A bit.

Bela was wearing a gorgeous black backless dress with stilettos. She was definitely overdressed for this place, and Sam deduced that, like him, she had misunderstood Kevin’s insinuation of the location.

But he wasn’t going to complain about it.

He paused a moment, a few feet away from her.

_Just walk up to up to her. Ask her what she’s drinking. Don’t freak._

Her back turned to him, Sam took another deep breath and stepped forward.

But that was when some other guy appeared at her side and rested his hand on her waist.

Sam froze. Thinking that was rather direct, almost too pushy, he waited a moment, hoping Bela would brush him off. In any case, Sam was severely considering that option himself.

Once she turned to the man, however, her face suddenly lit up and she gave him her brightest smile.

And Sam felt a pang in his chest.

Not knowing what else to do, he hastily walked past them, grateful that she hadn’t noticed him. At the other end of the counter, he paused a moment and glimpsed back at them with caution. Bela had her arms wrapped around his shoulders and leaned in for a kiss.

_Okay. This is bad. But maybe the situation isn’t as serious as it looks._

“God, I don’t know where she finds them,” said someone next to Sam, “but I’d very much like to know.”

Sam turned his head and was surprised to find Kip at his side.

_Great. This evening is just getting better and better._

And knowing it was probably a bad idea, he asked him, “What was that?”

“Bela and her boyfriends,” said Kip.

_Please, no._

“Boyfriend?”

“Yup. Patrick something.”

“How—how long have they been together?”

“A month or so, now, I think. Why?”

“No reason.” Sam swallowed hard and promptly turned towards the bar.

“You okay?”

_Good question._

Depressed and wanting nothing more than to flee this place, Sam eyed the exit.

_I should have never come here. It was a mistake and now I feel even worse than I felt before, if that’s possible._

And then, because of his crappy day, he decided to take advantage of his surroundings and signaled the bartender.

And moved on to the whiskey.

Sam then spent the better part of the next couple of hours gulping down drinks, trying as best he could to ignore the happy couple being disgustingly cute at the bar.

The truly interesting part of his evening, however, happened much later.

Sam eventually slowed down his roll. By then, he focused on the friends he had been sitting with, and with fun discussions, less alcohol, and a few timeouts outside, taking in the fresh air, Sam had started to noticeably sober up just before midnight.

Which was a good thing, because that was when he had made a new friend.

A new friend whom he had been very much enticed with.

Whom had made him laugh and blush.

And whom Sam had followed home.

Sam woke up the next morning to a mild headache. His throat was dry. One of his feet was cold. His whole body was heavy. Moving a muscle was too demanding.

The only comfort was the warm body glued to him.

Someone stirred. The mattress shifted weight. And Sam felt the warm body delicately leave his side.

A door opened.

And it was then, and only then, that Sam’s brain suddenly became alert.

As if he only just then realized the situation.

His eyes snapped open.

He slowly sat up and glanced around the room.

The bedroom was actually really nice. One brick wall with a weird folklore-looking painting hanging on it. A large window. A bunch of books in the corner of the room and two French doors (of different colors) with purple curtains.

But he had no idea whatsoever of where he was.

Of what had precisely happened the night before.

Of whose bed he was lying in.

And why he was practically naked.

_Though, that’s probably not difficult to guess._

_Shit._

He stumbled out of bed, practically falling off, only to suddenly freeze, letting out a groan of frustration. He wasn’t exactly steady on his legs, and it was difficult to say which between his heart or his head was spinning the most.

Once he felt stable enough, he peeked out of the window, hoping for a clue of his location. Alas, other than discovering that he was on the second floor of an apartment building, the view from the window did not bring much clarification on that matter.

Swallowing hard, he started walking around the bed, looking for his clothes.

Sadly, he didn’t find one piece of clothing. Nothing. A chill went down his spine, as he only had his underwear on, and the air was quite nippy.

He moved the sheets of the bed around, thinking his shirt and pants might have been tucked in there somewhere, but once again, he found nothing.

Defeated at the fact that his clothes must be elsewhere, he eyed the bedroom doors gravely.

He pushed open one door slowly. Stepping out of the bedroom, he found himself in a small cozy living room, where a green armchair and a grey loveseat were facing each other, with side tables resting next to them. Across the room was another door, probably leading to another bedroom, thought Sam. A large window was on his right, and on his left, once Sam tiptoed on the cold floor to have a better view, he saw the rest of the apartment, which consisted of a small dining room, occupied by a square table, next to a modest kitchen, where a kettle rested on the stove.

But still no one in sight.

He cleared his throat, and advancing slowly, he said, “Hello?”

Almost instantly, a door on his left, which he hadn’t noticed, flew open. A man with blond curvy hair and a gleeful face, appeared in front of him.

And the moment he set eyes on him, Sam remembered the rest of his night. The part which had been hazy to him a moment ago. And it came back to him like a rushing wave.

“Gabriel.”

He remembered how Gabriel had introduced himself in the later part of the evening. How they had conversed privately in their own booth. How Sam had practically stopped drinking by then.

How he had openly flirted with Gabriel. Danced with him, even—something Sam had always made a point of not doing. And of course, made out with him.

And they hadn’t even left the pub then.

And while Sam knew that his decision-making of the night before had been somewhat influenced by his unusual state of mind—considering that he had been slightly depressed and not exactly _sober_ —he was also very much aware that by the time he had hit on Gabriel, leaned in for a kiss—and this, quite shamelessly—alcohol had no longer been responsible for his behavior.

If anything, the only thing alcohol had brought to the table at that point was sleepiness.

Which had been when they had decided to leave the pub, and Sam had happily accepted Gabriel’s invitation.

He remembered it. Clear as day. And the memory made his heart jump.

Which was a surprise to Sam.

“Sam. Hey, you’re up,” he said, smiling.

They exchanged awkward, yet warm, looks, processing it all.

The only problem was that just as Sam was remembering Gabriel’s touch on him, and barely assessing how he felt about it now that the morning was here, something else happened that complicated the situation _slightly_ for him.

Someone else appeared next to them.

“Sam? What are you doing here?”

Turning briskly to his right, Sam felt his heart stop.

“Bela?”

She stepped towards them, holding down a grin as her eyes bounced between the two.

“I wasn’t aware you knew my roommate, Sam,” she said.

_Roommate?_

At Sam's silence, Gabriel replied, “We, um, got to know each other last night.”

“Plenty of knowing by the looks of it too,” she said. “Especially with those boxers of yours, Sam.”

And then, as if the situation wasn’t embarrassing enough, Sam looked down and noticed he was wearing his pair of golden boxers.

The ones Dean had given him last Christmas as a joke.

The ones with mistletoe printed on it.

Strategically located mistletoe.

Lifting his head, Sam let out an awkward laugh. He crossed his arms over his chest, then lowered them as smoothly as possible, trying casually to cover himself, even though he knew very well it was pointless.

_I want to fucking die._

And then, under Bela and Gabriel’s amused stares, he promised himself he would kill Dean next time he saw him for having given him such a stupid present.

Or, as it turned out, the poor advice of going out.

**Notes for the Chapter:**

> Here is the third chapter! a little later in the day than I had planned but it's still December third where I'm from lol no matter what the site says lol.  
> Hope you enjoy it!! Have a nice evening everyone!


	4. Chapter Four: The Morning After

“I’ll leave you two chaps to have a bit of privacy for…whatever discussion is about to unfold,” said Bela after a long minute of silence. “Gabe, I was actually on my way to let you know that Patrick has his car. He knows you work around the same area, so he’ll drive you if you want, ya?”

“Great. Thanks.”

She nodded at them both and headed towards the other room, the one facing Gabriel’s.

“How are you feeling this morning?” asked Gabriel in a genuine tone.

“Okay. I mean, I—” Sam cleared his throat. “Where are my clothes?”

“Oh, right. Hold on, I’ll get them.” He turned on his heels and disappeared to where he had come from, which Sam could only guess was the bathroom. 

Gabriel reappeared, holding a pair of jeans, an undershirt and Sam’s plaid shirt.

“I wondered if it would have time to dry properly if we hung it in there, but—”

“Why did—did it need to be washed?”

Gabriel frowned. “Yeah. Someone at the club spilled an entire pitcher of sangria on you.” He handed Sam his clothes, lifting an eyebrow.

_That sounds…vaguely familiar._

_Wait. I remember laughing my head off while looking down at my clothes. My wet clothes._

_And going to the bathroom, sponging it all out as best I could with cheap paper towel. And then awkwardly standing in front of the hand dryers._

“When we got here,” continued Gabriel, “we cleaned—you don’t remember?”

_Right. We cleaned my clothes._

_Because I said they were sticky._

_And I undressed myself._

_Literally as I stepped into this place._

_And Gabriel kindly offered me a large shirt to sleep in._

_But I told him that would be counter-productive._

_That’s what I said._

_Counter-fucking-productive._

_Great._

_I’m not allowed to ever go out again._

“Um, most of it is coming back to me now that you’re saying it. I’ll—I’ll just—” he said, lifting the clothes as explanation.

Gabriel nodded, and Sam dashed to the bedroom to get dressed, as if he needed privacy to do this.

Once he stepped into the bedroom though, he felt stupid for having done so. Not only had the bathroom been right next to where he had been standing, which would have been more than suitable for him to use, but now, all he could do was to stare at the bed.

As the memories of the night before kept coming back to him.

Flashes. Of tingles. Exploring hands. And soft breaths.

And his lips—

Sam cleared his throat. He dressed himself quickly, despite still feeling shaky. As he was putting on his shirt, his eyes fell on the nightstand to the right. The side where Sam had been sleeping. There was a large glass of water and his phone.

Sam grabbed it.

Two missed calls from Dean, as well as five text messages.

All from the night before.

A soft knock against the door was heard.

Sam turned around briskly and found Gabriel in the doorway. 

“Sorry, I didn’t mean to scare you. Here,” he said, offering him a cup of coffee. “I think that might help.”

“Thanks.” He shoved his phone in his pocket and picked up the cup, taking in the smell of bold coffee.

Not sure where to begin, they both stared at each other quietly for a moment, until Gabriel said, “So, you know Bela.”

“We work together.” Sam blew on his coffee, giving himself an excuse to avoid Gabriel’s eyes in that moment.

“Right. Which is how you know Kevin too. You briefly mentioned he was your friend, but I hadn’t realized what you meant. I feel kind of silly to not have put two and two together.”

“Don’t be,” said Sam, turning to him. “I’m the one who should have been more specific. Wait—you know Kevin?”

“I’ve met him before. Bela sometimes invites me to her office parties. Or just whenever she goes out.”

“Like last night.”

“Yeah. She texted me the address once she got there. I wasn’t planning on going because I had a really long day at work, but once I was out of there, I decided I wasn’t that tired. So, I thought I could swing by for a while. Anyway, I—yesterday, I recognized some of her co-workers, but I didn’t remember seeing you before. And as far as I knew, it wasn’t an office outing, so...”

“It wasn’t,” Sam reassured him. “And I rarely attend office parties or—I—I just can’t believe we never got on the subject last night.”

“Well, we were slightly distracted,” said Gabriel, amused.

Sam laughed shyly with him.

They became quiet again, exchanging an awkward look.

“I just—I feel like I need to clarify that nothing happened,” said Gabriel, pointing at the bed. “Well, okay. Maybe not ‘nothing,’” he said, gesturing air quotes. “But we didn’t…”

Sam nodded. “I know. We—I—I remember now. After we, um, took care of my clothes, we went to bed because I said I was cold.”

“You certainly did,” said Gabriel, laughing.

“And I—I remember a few things but…I’m not really sure after that, though.”

“That’s because you fell asleep.”

Sam gaped at him. “That’s…embarrassing,” he said, running one hand over his face. “I feel like I have to apologize.”

“Don’t. It wasn’t like—there’s no need to apologize. You were tired. We just lay down, talked a bit—”

“ _Just_ talked?” said Sam, lifting an eyebrow, suddenly remembering something.

“A few things more, perhaps,” said Gabriel, smirking. “But not—how may I put this…we didn’t do anything that would be deemed _too_ indecent if we would have been caught in public…”

Smiling, Sam said, “Of what I remember, though, it was slowly getting there, right?”

“Slowly," said Gabriel with a grin on his face. "But then we started talking again, and it was clear that sleep was getting the better of you. And to be honest, I wasn’t very far behind you on that. So, we just…”

“Fell asleep.” Sam blew on his coffee before taking a sip. The taste was strong and coarse. He then felt the need to say, “Sorry, I’m really slow this morning. It’s really unlike me and I think that’s doubly confusing me.”

“There’s no problem.”

“I’m just saying this so you know that I remember. Like I wasn’t—I didn’t black out or anything.”

Gabriel, understanding what Sam was getting at, said, “How do you feel about it this morning?”

Sam, exhaling in relief, sat down at the edge of the bed.

Truth be told, Sam was struggling. He didn’t feel bad about the night before. Embarrassed about certain parts, perhaps, but he didn’t have a pit in his stomach or a dreadful feeling that something had gone wrong.

From the moment that Gabriel had showed up, everything else that had followed, Sam had zero complains about.

Thinking about the laughter they shared, as well as the kisses and touches, however briefly, he couldn’t help but smile.

And every time he glanced at him, Sam actually had a good feeling about him.

Until he remembered Bela.

And that Gabriel was her roommate.

Which complicated everything.

“Sam? I’m gonna go right ahead and say that I enjoyed last night. And I’d very much like to see you again. What about you?”

Gabriel was giving him the look. The look that so many—including Sam—yearned to see. The damn look that was borderline pleading for someone to extend their stay. To spend the day with him and relax. As though he was about to make him breakfast in bed like in the goddamn movies, making him think for a moment that Sam didn’t need to look any further.

And Sam almost went for it. The temptation was real.

But as much as he hated seeing it like this, the fact remained that Gabriel was not Bela. And that detail made a great deal of difference for Sam.

Even if he knew that Bela wasn’t single.

Even if he knew that his chances had probably decreased now that she had caught him with her roommate.

At the end of the day, however charming Gabriel was, Sam was still pining for her.

So, no. Sam concluded that this, whatever this was, was a bad idea.

“Um, I—I—thank you for last night. And I would, but the thing is—” Sam couldn’t finish his sentence.

“It’s okay,” said Gabriel, adopting an earnest tone. “Don’t worry. I get it and I still enjoyed last night either way.”

Sam shut his mouth, feeling a considerable amount of guilt rising.

Gabriel stood up from the bed, but Sam reached out for his arm. “Wait, wait,” he said as gently as he could. “I—I need to explain something. I enjoyed last night too. Very much. And I—but you caught me at a bad time. I just—I’m kinda into someone, but it’s compli—and—” he paused, weighing on his words. “And I—I’m sorry.”

“All right. No offence taken, I swear. But, like, I had to try. I mean,” he said, gesturing at Sam.

Sam nodded, almost blushing. “Thanks. I’m flattered. Really. And you’re—I can honestly say that you greatly improved my night.”

“It was my pleasure.”

A brief moment of silence passed, during which Sam was growing more anxious at Gabriel’s silence.

“Okay, well, I guess I should probably…go.”

He handed him back his cup and made his way to the door. He put on his boots and his coat, as Gabriel was patiently waiting for him. Sam opened the door and just awkwardly waved at him. But before he left, Gabriel said, “Sam? Can I just say two more things before you leave?”

He nodded.

“I don’t know what’s the situation, but I hope that, whoever you’re waiting for, they wake up pretty soon.”

Sam felt a pang in his chest. “Thanks.” He gave him a shy smile. He waited for Gabriel to continue, but he remained silent. “What’s the other thing?” asked Sam finally.

“Oh. Where on earth did you find that pair of boxers? Because I have to say, I approve of your style.”

Sam dropped his head, laughing and feeling embarrassed. “Those were a silly gift from my brother who thinks he’s very funny. I nearly never wear them, because…well…”

Gabriel, smirking, said, “I may be utterly biased here, but speaking as someone who got to, um, admire them on you, one of the few, it seems, I think you ought to rethink your opinion on that matter.”

Sam did his best to keep his face straight as he nodded to him. “Don’t hold your breath, but I’ll take it into consideration.”

“Good.”

And Gabriel looked like he was about to add something else, but he then crossed his arms and gave him a short nod as a send off.

Sam imitated him and turned away. He dashed towards the hallway, feeling simultaneously relieved and upset at that fact.

**Notes for the Chapter:**

> As always, thank you for reading! I hope you enjoy Sam and Gabe's little morning talk lol!  
> Have a nice evening!


	5. Chapter Five: Dean's Christmas Plan

Dean, who was laughing so hard it made his stomach hurt, had to lower his phone a minute to catch his breath.

“Dean. Dean? Dean, damn it! Stop laughing,” Sam was yelling through the phone. “It’s not funny!”

With tears nearly forming in his eyes, Dean took a deep breath and put the phone back to his ear, still giggling. “Sorry—I’m sorry.” He paused a second, exhaling. “It’s just—her roommate?” he said, before starting to laugh again. “And the mistletoe boxers? This could only happen to you.”

“Yeah. Thanks for that by the way.”

“You’re very welcome, Sammy.”

“God! You’re such an asshole. I knew I shouldn’t have said anything. You do realize that everything is a mess now? I mean, the point I’m trying to make here is that she’s dating someone. And it’s not _me_.”

Dean took another deep breath to really stop laughing. “Okay, I’m—I’m sorry about that. I know it sucks.” And then his grin was back on his face. “But hey…the night wasn’t a total loss…far from it. You didn’t _come_ back empty handed. It’s like they say, ‘When a door closes, a window opens.’” And unable to help himself, Dean added, “And in this case, what opened up was—”

“Dean, I swear to God, do not finish that sentence! And nothing happened!”

And Dean was lost to another fit of laughter. Once he regained his composure, he drew a breath. “Aw, Sam. Thanks for telling me this. This is great.”

“No. This was so embarrassing. And awkward. Thank God he was actually decent and that he didn’t make a big deal about it either.”

“What do you mean?”

“He sort of asked me out.”

“He did?” said Dean, delighted at the idea. “I like him. _Please_ , tell me you said yes.”

“Um, no. Obviously not, Dean.”

“What? Why not?”

“Um, because of Bela,” said Sam as if it was the most obvious thing in the world. “Who is the one I like, remember?”

“Ugh,” groaned Dean. “Why do you always go for the mean girls, Sam? Why not change it up for once?”

“I don’t do that,” he said, offended.

“Right. Amelia. _Ruby_.”

“Amelia wasn’t mean.”

“She kinda was, actually.”

“Whatever. It doesn’t change that I like Bela. And even if Gabriel was…he’s her roommate, Dean. I—I can’t.”

Dean pursed his lips. “Sam, I just—I was just thinking…” Dean had begun saying, but then he decided against finishing his sentence.

“What?”

“No, never mind.”

“Dean, what?”

“I—okay, yesterday, I thought about what you said. That you— _we_ won’t be able to spend Christmas like we usually do.”

“I’m sorry—”

“Don’t, Sam. It’s okay. I told you. This isn’t on you. And I wasn’t saying this for that.”

“Okay,” said Sam in an uncertain tone. “Then, what?”

“I was just thinking that since we won’t be able to spend Christmas together, it doesn’t mean we should spend it alone.”

He left it at that for now. There was a long pause and then Sam said, “Dean, I swear I’ll be okay on my own. And I’m sure Bobby or Charlie won’t leave you alone if that’s what you’re worried about. Jo will probably crash at your apartment on principle.”

Dean laughed at the thought. “You’re probably right about that. I—I know I have options. But…that’s not what I was getting at. But—now that you said that, I feel ungrateful to not have looked at it that way and—”

“Dean. What were you going to say?”

He took a deep breath and said, “Look, no matter what happens, I know we’ll be fine. But I have to admit that I would feel bad knowing you’d be by yourself.”

“Dean,” said Sam, laughing, “I said I’ll be fine. I promise I won’t be mad if you end up having a great holiday without me. Even if I’m on my own. If anything, I’ll be relieved for you.”

“That’s just my point, Sam. It’s the same for me. I’d much prefer to know you’d be with someone.”

He heard Sam sigh on the other end of the line, knowing full well that Sam couldn’t argue against that.

“So, I—I was thinking,” he continued, “since we know it’s going to be different this year, why not take the occasion to—to find someone to spend it with. As in, a _special_ _someone_.”

“I see.” Dean could tell Sam was smiling. “I’m not gonna add you in my sad boat here, Dean, but just out of curiosity, given that I already have difficulty finding said _special someone_ on a regular basis, what makes you think I can pull this off within a few weeks? And,” he added urgently, “if you say by a Christmas miracle, I’m hanging up. I’m all out of those, apparently.”

“Yeah, well, we _are_ kind of in the same boat on that one. And I know it’s probably unlikely, but would it kill us to try, though?”

Sam sighed. “Probably not. No.”

Glad that Sam agreed to that part, at least, Dean yielded the conversation back on topic. “Great. So, with that in mind, what are you going to do now?”

“What can I do? Bela is dating this Patrick guy. Unless she breaks up with him…and assuming she’s even interested or that she doesn’t have any other plans—”

“I didn’t mean about Bela, you moron. I meant the guy. Gabriel. Gabe.”

Sam groaned. “Dean, no. I told you. This is not a good idea.”

“But—”

“What about you?” said Sam, evidently done with that part of the conversation. “What are you going to do?”

_Damn it, Sam. I’m trying to help you._

“Dean? Do you have someone in mind?”

He wasn’t ready to let Sam discard the possibility of Gabriel any time soon. But considering how stubborn his brother was about it in that moment, Dean opted to wait for now, knowing that there would be plenty of time to revisit the idea before Christmas. Thusly, Dean moved on to his side of news.

“Um,” Dean cleared his throat. “Maybe…yes.”

“Wait, really? Who?”

“It’s probably not gonna—”

“DEAN, who?”

“I—okay, that’s why I was calling you yesterday. When you were…busy,” he said, grinning.

“I’m ignoring that and I’m literally dying at the edge of my seat here. Tell me.”

“So, you’ll never guess who I’ve been paired up with at the Wrapping Booth.” A few minutes later, Dean had recounted his events of the afternoon before, with great enthusiasm. How Castiel was as handsome as he had remembered. How he was even nicer than Dean had hoped.

“That’s so awesome, Dean,” said Sam. “So, when are you going out? Since Christmas is the endgame and all, I’m guessing you already have something set up leading to that.”

“I—I haven’t asked him yet.”

“Excuse me, what?”

“I’m working on it,” he said defensively. “I didn’t want to sound too desperate yesterday. I have to wait for the right moment so I don’t look like a freak. I don’t even know if he’s single.”

There was a short pause.

“Un-freaking-believable,” laughed Sam.

“What?”

“Dean, you’ve been on my case forever about me stalling with Bela and now Cas—the guy you’ve been pining over for like a year—”

“I wasn’t pining!”

“—comes around like magic and you do nothing?”

“Okay, okay. I—I will. And I was just trying not to be too insistent. I will have to work with the guy for the next few weeks.”

“How is that any different than what I was— _am_ —doing with Bela? I work with her _everyday_.”

_Shit. Maybe Sam is right and I did go a little hard on him._

_But then…._

“No. You’ve been working with her for over six months. I officially met Cas yesterday. _Difference._ ”

“Just—take it from someone who knows, don’t wait too long.”

“I won’t. And since you got lucky, maybe I should wear _my_ mistletoe boxers. See what happens.”

“God. One, I told you nothing actually happened.”

“HA. Right. ”

“Nothing. Happened. And bye.”

“All right, all right. I have to go anyway. I’ll call you back after my shift. Unless you’re still busy showing off your underwear—”

“BYE.”

Laughing, Dean hung up. He checked the time and realized he would have to leave within five minutes or he would get into trouble. He grabbed his cold toast, gulped down his coffee as fast as he could, which prompted him to make a face of disgust once he had done so, and seized his jacket and keys before rushing out of the door.

Dean had been in a good mood all morning. And this had been well before Sam’s phone call.

He was, for the first time in a really long time, truly looking forward to going to work. While he always loved working at the garage, as well as with his co-workers there, especially Bobby and Ash, he had to admit that he had certainly never _trotted_ to work with a smile on his face at the prospect of finding them there, though.

Once at _The Milton’s_ , however, he was slightly disappointed to see that the booth was empty. Guessing that Castiel must be running a little late, he simply set up everything, while having the firm belief that it would most likely be pointless—as it had been so for the past week.

He waited patiently, returned smiles to the customers who saluted him in the same fashion, and was grateful that someone had managed to change the music playing all over the store. Though, he was sure that it would only be a short respite.

Finally, Castiel joined Dean in the booth.

“Sorry, I ran into Rowena and she was just giving me additional information she felt that I needed but had failed to do so yesterday.”

“S’okay. Everything all right?” asked Dean.

Castiel’s answer was a simple nod.

And then he turned around and silently helped Dean with setting up the material they needed.

For the rest of the afternoon, Castiel was incredibly nice and polite, in a genuine manner, to the customers (which they happened to have, unlike the day before) and to Dean as well. He questioned Dean on countless subjects, from his favourite food to his job at the garage.

But never anything overly personal.

Almost as if he was purposely avoiding deep topics and wanted to keep things simple.

And he managed to skillfully do so by taking the lead on their conversation. He was asking the questions and he listened.

But he himself shared very few details about himself.

A fact that was somewhat alarming to Dean. This was the opposite of how he wished things between them to progress.

And while Castiel hadn’t expressed any discomfort, verbally or not, compared to the day before, all this made him seem guarded.

To the point where Dean wondered if he had said anything wrong. Or had misread their previous afternoon.

Trying to not panic or make wrongful assumptions, Dean decided to follow Castiel’s lead for now, as the last thing he wanted was to render Castiel uncomfortable.

So they continued wrapping presents (and practicing the stylish methods), while exchanging a few words when they could.

And Dean attempted as best he could to keep the lingering looks to a minimum.

Which turned out to be a difficult task.

By the end of the afternoon, Castiel had skillfully perfected all the patterns from the document Dean had been handed. And with them seemingly busy wrapping presents—not to mention the impressive style of the ones Castiel had done—it had generated attention with the customers and more people had shown up to the booth in one hour than since Dean had started working there.

While Castiel was finishing up an intricate wrapping, which, once he had put all three packages together, would form a cute snowman, Dean couldn’t help but look at him, as fascinated as the customers were to see him at work. Once he realized he was staring, he refocused his attention on his own task.

But not being as crafty as Castiel was, he felt the pressure of disappointing certain customers rising within him under their watchful stare.

It also didn’t help that his mind kept circulating back to the same dreadful thoughts.

_Maybe he’s taken._

_Maybe he’s just not looking right now._

_Or maybe he’s being cautious and doesn’t want to rush into anything._

Dean sighed deeply, keeping his eyes on the schema of a complex bow.

_And if he really is giving me a brush-off, I can’t really do anything about it, except to accept it._

And with this, as if Castiel had read his mind, and just as Dean was beginning to think that his idea about him and Sam making alternative Christmas plans had been ridiculously wishful thinking on his part, he suddenly felt Castiel’s gentle hand on his back.

Dean turned his head and found Castiel, with a shy smile on his face, standing right next to him.

Done with his wrapping, Castiel had apparently been watching Dean work.

Dean cleared his throat and shifted on his feet. “I’m—I think I need a little more practice than you for this one.”

“That’s perfectly fine. I’ll help you with the bow and you take care of the rest if you want?” he said kindly.

Looking him straight in the eye, Dean nodded. “Thank you.”

He slid it towards Castiel and they continued working side by side.

With their elbows touching.

**Notes for the Chapter:**

> Thanks for reading!! Hope you enjoyed this chapter!! More tomorrow!!  
> Have a nice night!
> 
> (and thank you to Dancia and Landrala!!)


	6. Chapter Six: A Merry Encounter

The next few days at work were a bit challenging for Sam. Given that a numerous amount of his co-workers had apparently showed up at the bar—during the part of the evening that was still eluding him, at least—the word that Sam Winchester, the straight and narrow of the office, was in fact a heavy partyer had spread like wild fire.

The worst part, as it was often the case in instances such as this one, was that nearly everything that had been reported was actually false.

If everything was to be believed, Sam had supposedly danced _on_ the bar, scored the bartender’s number, made out (and more) with up to seven different people (notably a pretty brunette, a petite red head, a brawny dude, and so on), and while no one seemed to agree on whom he had gone home with, the most popular—and outrageous—story was the one where Sam had taken off in a limo with a member of a royal family.

But none of Sam’s co-workers who had been present, not one single person, had mentioned anything about Gabriel, or described someone matching his description.

Which Sam had thought rather odd as he remembered passing a considerable amount of time with Gabriel _at_ the bar, surrounded by people he knew and had indeed interacted with them.

Including Kevin. But after a quick chat with his friend, Sam learned that Kevin was hazy on many details from that night, not just Sam’s choice in companionship.

Which left only one person other than Sam who knew the truth: Bela.

Sam wasn’t sure if her silence on the matter was a good thing or not. On the one hand, as far as he knew, she had been one of the rare people of the office to not spread any stories, which Sam appreciated greatly.

On the other, stating flatly what she knew would have obviously stopped everyone’s gossip.

Of course, none of this was her business, and Sam was, above all, the one person who should clarify the situation. Not Bela.

But he couldn’t find it in himself to do it. Mostly because no one had addressed any questions to him directly, so it felt rather odd to bring up the subject out of the blue, especially when he didn’t even want to talk about it in the first place.

And now, Sam perceived a distinct shift in everyone’s mood at work whenever he would step into a room.

When he had mentioned the issue to Kevin, his friend told him that besides the annoying gossiping, which he claimed would die down soon enough, he hadn’t noticed anything else like what Sam was suggesting, and told him it was most likely all in Sam’s head.

An idea, as frustrating as it was, that had been shared with Dean, once Sam had called him during his lunch hour on the Wednesday.

“I’m sure everything is fine, Sam,” Dean assured him.

Sam let out a deep sigh. “You’re probably right. It’s just…I’m not used to this and it makes me uncomfortable.”

“It will go away. If it’s even there at all.”

“Yeah.” And then, wishing to change the subject, Sam cleared his throat and asked Dean what had occurred when he had asked Castiel out.

“I, um, I haven’t yet.”

“What? Why?”

“I—it didn’t feel right.”

“How come? What happened?”

“Nothing. I just…it didn’t feel like the right time. That’s all.”

And although this was a perfectly good answer, Sam didn’t like it and strongly suspected that Dean was hiding something from him.

“Dean,” he said, adopting a serious tone. “Why did you hesitate? Did something happen?”

He heard Dean let out a deep sigh and say, “He seemed…distant.”

Sam frowned. “What do you mean?”

“I—I don’t know. He wasn’t rude or anything. Just, like, I don’t know how to explain it. But he wasn’t like the day before. It ended on a good note, though, but… I, um, don’t want to mess it up, so I thought waiting would be best.”

Sam was stunned. Dean typically moved faster than this whenever dating was involved.

“Okay,” said Sam. “So, you’ll just ask him tonight, then?”

“Cas doesn’t work on Wednesdays.”

Sam sighed. “All right, well, I hope tomorrow is better.”

“Yeah. Tomorrow.”

The rest of the day, though uneventful, had still been rather grim for Sam. He avoided Bela every chance he got out of embarrassment, which unfortunately felt very contradictory to what he really wanted.

Thus, after a long day of work, Sam dragged his feet out of the office, long after nearly everyone had left, and exited the building with a low spirit.

Fluffy snow was falling and the weather was mild.

Sam stared at his phone for an instant, and instead of ordering himself an Uber, even if he might regret it later, he shoved his phone in his pocket and began walking down the street.

He had no desire to return to an empty apartment right away, and so, he decided to stay out.

And the next thing he knew, he found himself at the entrance of an old movie theatre. He purchased a ticket for the next showing, whatever the movie was, bought himself a large popcorn and a drink, and found himself a seat in a nearly empty theatre.

The movie, it turned out, was a foreign movie. An _old_ foreign movie. Italian, at that, as far as Sam could deduce.

A smile appeared on his lips, he sunk himself in his seat and watched with attention.

Having had no expectations, Sam thoroughly enjoyed the feature and was incredibly glad of his impulse.

Although the film had been incredibly sad (tears had been shed), it had nonetheless managed to cheer him up. It was this odd feeling of having enjoyed something so much that it had left you feeling whole, even though you had endured some sorrow through it all, thought Sam.

In a merry mood, he threw his empty bag and cup into the garbage, went to the bathroom quickly and then headed to the exit.

He took a deep inhale of winter air and stood there quietly for a moment with a smile on his face. Knowing it was time to return home, he reached for his phone in his coat pocket.

He then heard someone call his name.

Gabriel was standing a few feet away from him with a surprised, yet cheerful, look on his face.

“Gabriel? What are—hey!”

“Hey, back,” he answered. “I thought it was you, but I wasn’t sure.”

“What are you doing here?” said Sam, returning his smile.

“I’m meeting a couple of my friends. We’re supposed to go see _Metropolis_ ,” he said, pointing at the door of the movie theatre. “What about you?”

“Just finished one. Not _Metropolis_. _Umberto D_.”

“And? Good?”

“Yeah, actually. Like, soul-crushing, but good.”

“I like those.”

Sam nodded awkwardly. He waited a moment, and then said, “Well, I don’t want to keep you from your friends.”

“You’re welcome to join us,” blurted out Gabriel. And then, as if he had just realized what he had said, he added, “But you just watched a movie, so you might not be up for another one right now…”

Sam let out a small laugh. “Maybe not. I have to head out. This was…spontaneous of me. I’ll probably regret it tomorrow morning.”

Gabriel nodded understandingly. Sam, however, had discerned a hint disappointment in his eyes.

Causing Sam to feel a pang of guilt in his gut.

“I hope you enjoy your movie with your friends,” said Sam as genuinely as possible. “And it was nice seeing you.”

“Same,” said Gabriel, beaming at him. He took one step towards the doors, but stopped and turned back. “What if I suggest that we meet here in the future to watch another movie together, then?”

Sam bit on his lips, holding a smile. “You mean like a date?”

“I didn’t say a _date_ ,” replied Gabriel, faking defensiveness. “But if that’s what you want, you know I’m all for it.”

Sam had to laugh at that. “I see.”

“So?”

Sam took a moment to ponder on Gabriel’s invitation, but his response remained the same as the last time.

“I’m sorry. I—what I said the other day, I wasn’t lying. It wasn’t an excuse. I really am into someone else. That hasn’t changed and I think—I’m not sure this is a good idea. I am, again, flattered though.”

“Hmm,” said Gabriel. “All right. If the handsome gentleman said no, I have to respect that.”

“Thanks,” laughed Sam.

“Good night, Sam.”

“Night,” Sam said and watched Gabriel disappear behind the doors of the movie theatre.

And tried to ignore that little voice inside his head telling him he had made a mistake.

**Notes for the Chapter:**

> Thank you for reading!! Hope you have a nice evening!! 
> 
> (Thanks to Danica and Landrala!!)


	7. Chapter Seven: And Promising Chats

Over the next few days following his random encounter with Gabriel at the movie theatre, Sam had quite inexplicably run into him on three more instances.

Twice on the Friday and once on Saturday morning.

He had bumped into him at a twenty-four-hour convenient store on his way to work.

He had encountered him at a bistro that Kevin had dragged him to across town during lunch.

And on his Saturday morning run, he had spotted Gabriel across the street, waiting for the bus.

Due to their equally busy schedule, however, their interactions had been brief. Quick greetings and chitchat were exchanged, followed by goodbyes.

And yet, it would be important to mention that Gabriel had still taken the opportunity to renew his invitation to Sam.

On all three instances.

He had casually asked Sam to dinner. For a night walk. For coffee.

And with every encounter, Sam had to admit that it was becoming more and more difficult to decline Gabriel’s invitation. His tenacity was always somehow graceful and charming, but never nagging. And he was always respectful of Sam’s choice and never made him feel bad for refusing.

And Sam was starting to wonder why on earth he was turning him down in the first place.

And yet, since his circumstances had not changed, he always did.

Even if he had fully regretted it that last time.

As for Dean, he had been thrilled to find Castiel jubilant and chatty on Thursday night.

It seemed that whatever might have bothered him on the Sunday before was now history.

 _Maybe he just had a bad day._ _Something that can happen to anyone. I, for one, am certainly aware of that fact._

But the change was so flagrant, Dean was now wondering if he had not imagined it in the first place.

Perhaps, he concluded, he had simply projected his own insecurities onto Castiel’s behavior.

In the end, he tried to put the matter to rest and focus instead on his evening and enjoy working alongside Castiel.

And even if the night hadn’t offered many occasions to converse freely, as they had had the week before, Dean, having the pleasure of glancing at Castiel’s smile whenever he could, had found nothing to complain about.

The same occurred on the Friday.

But by Saturday, while he was immensely enjoying Castiel’s company, Dean realized that a whole week had passed, and he still didn’t know much about Castiel.

About his family or work, save the very brief details he had shared the day they had met.

Which had been why Dean had done a quick search online once he had learned that Castiel’s last name was Novak.

“You cyber-stalked him?” Sam had said, exasperated, when Dean had told him. “Dean, for God's sake.”

“I didn’t. I just checked for him on social media. That’s all. That’s literally what it’s for, Sam.”

Sam’s only response had been a loud sigh.

“I was just curious. And it doesn’t really matter because I hardly found out anything.”

“He’s not on there?”

“No, he is. He friended me and everything. But I don’t think social media is his thing. He barely posts anything.”

“Dean, here’s a crazy idea: you know how you could learn more about him? _By asking him out_.”

Which, of course, Dean still hadn’t done.

Nor had he even come close to finding out if Castiel was seeing anyone.

Nor have a distinct impression if Castiel would be interested in him for that matter.

And with the few opportunities they had had to have a proper conversation—and a private one at that—it didn’t seem like Dean would find out any time soon.

Unless Dean finally did something about it.

Thus, on that Saturday afternoon, he had then set his mind to, at the very least, exchange a few words with Castiel _after_ their shift.

_Even if I have to seriously haul ass to my other job._

_It will be tough._

_But I’ll make due._

Alas, once Dean and Castiel had left the booth to Garth and Alicia at the end of their shift, Dean, on the way to the employee lounge, after being stopped by customers and co-coworkers, had somehow lost track of Castiel.

Almost as if he had mysteriously vanished.

Which Dean had thought was very odd.

Either way, Dean grabbed his stuff and coat, and did a quick tour of the store before leaving in the hope of spotting him, but without success.

Things improved on the next day, however. Mainly due to a storm, Sunday afternoon turned out to be rather calm at the store.

Customers were still to be tended to, obviously, but there had been moments of respite, which had made it easier for Dean and Castiel to converse more casually than they had had the occasion to do over the past couple of days.

Finally.

And Dean was not going to waste it.

“What are your plans for the holidays?” he asked. “Anything special?”

Castiel leaned on the counter, letting out a loud sigh. “No. Not really. Same old.”

“Which is?”

He hesitated a moment, but then said, “Just surviving Christmas among my family.”

“You guys don’t get along?”

Castiel lifted his eyes, tilting his head. “We don’t always agree, no. And this, on too many subjects for my liking. And given that we are a large group, it comes to be unbearable rather quickly.”

Dean frowned. “A large group? How many of you are there?”

“I have four siblings, who are, quite frankly, aggravating. My parents are…I don’t even know where to start with that. And then, there are my aunt and uncle, and their kids—my cousins—eight of them.”

“ _Eight_?”

“Yes. And some of them brings friends and—like I said, _large group_ ,” he sighed. “And—anyway, they aren’t _all_ bad, but it gets to be quite taxing. I tend to avoid the many family gatherings in this time of year as much as I can to limit the ‘trauma,’” he said, gesturing air quotes, while half-laughing. “This year though, I don’t think I’ll be able to skip any of those since I came back to Lawrence much earlier than I usually do.”

Dean didn’t know what he had expected, but that hadn’t been it.

“I’m sorry this is such a bad time for you.”

“Well, it’s the holidays. What else is new?” he said mockingly.

Dean nodded blankly, not knowing what else to say. Even though he was slightly disappointed to hear that Castiel had, indeed, plans for the holidays, which he had suspected, he was even more desolate to learn that the holidays were such a pain to live through for Castiel.

“What about you?” asked Castiel. “How do you usually spend your holidays?”

_Okay._

_Let’s just see where this goes._

_Chill, though._

_He did just say he has plans and isn’t even that found of the holidays after all._

“Oh, um, it’s usually just me and my younger brother Sam.”

The moment the words came out of his mouth, he hoped to leave the matter there.

Getting caught on that topic this early on, and especially at work, was not what Dean had intended.

At Castiel’s questioning expression, however, Dean knew he needed to elaborate a little more on the subject.

So, after a quick glance around them, detecting no potential customers—or eavesdroppers—Dean, took a deep breath and started to speak.

“My parents passed away years ago. Car accident. And it’s just us, no grandparents or uncles and aunts. So, Sam and I usually try to make a point of doing something for the holidays together, but it’s getting more complicated every year.”

“Dean, I’m—I’m so sorry—”

“Don’t—you—it’s okay,” he said, waving his hand. “Thank you. But it happened a long time ago. And we do have close friends who are like family too. My boss at the garage actually. So, we’re okay.”

But Castiel was not convinced. “Still. Now I feel awful. Complaining about how insufferable my _large crowded_ family is, when you—I—”

“It’s okay. I promise. Look, if you say they are insufferable, I believe you,” he said, laughing awkwardly. He paused a moment, weighing if he should continue or not. But one glance at Castiel’s kind eyes, and Dean found himself saying, “And I—it’s really weird to say this, but, in a way, I feel like Sam and I wouldn’t be as close to each other if it hadn’t been for what happened. It sounds horrible to say it like this, and obviously, in a perfect world, I’d much prefer the version where my parents lived a long and happy life over this. But Sam and I, we are very different from each other, and even though I always cared for the little nerd, I don’t think I realized how much I cared until after it happened, you know?”

Castiel nodded, listening attentively.

Feeling like he was dangerously over-sharing, Dean cleared his throat. “Anyway, to go back to your question, it’s usually just Sam and me. We hang out. Eat a lot of food. Watch Christmas movies. I mean, think couch potatoes and not being ashamed of it.”

Castiel laughed. “That sounds great. Wait—why do you say ‘usually’ though?”

_Chill._

“Um, it doesn’t seem like we will be able to do so this year. Sam doesn’t live in Lawrence. And while he had been able—by some miracle—to always make it for Christmas in the past, it doesn’t seem like he will this year.”

Dean drew a quick breath, and just as he was summoning the nerves to lean the conversation towards a very specific question, Castiel asked, “Where does Sam live?”

“Chicago. He works for the Sandover firm.”

“Lawyer?”

Dean nodded proudly.

“Was this his first choice? The firm, I mean. Not the profession.”

“Not really. It has an impressive rep, that’s not the problem.”

“Then what is?”

“The location. That wasn’t exactly where he was hoping to settle.”

Castiel smiled at him. “It’s far from here. From you.”

Dean nodded, lowering his head a moment. “It goes both ways though. You said it yourself when we met: a mechanic is a useful trade and needed anywhere.”

“But it would still entail uprooting your entire life. And even if Sam would be there, moving isn’t cheap.”

“You’re right about that,” he said, laughing.

“Have you ever considered it?”

“Moving? Nah. Not really. I’m not opposed to the idea, but I don’t know. This is home.”

Castiel beamed at him. And then, his smile widened even more. He leaned his head backwards as if an idea just occurred to him.

“So, Sam lives in Chicago, right?” Dean nodded. “You should tell him to make a stop at a bakery. It’s called _The Sweet Spot_. My—a friend—an old friend of mine works there.”

“Yeah?”

“It’s very delicious. I’ve been there myself every time I had the chance to be in the neighborhood.”

“And this happens often?”

“No. Not as often as I’d like. But you should tell Sam to look it up. It’s definitely worth the trip. I’ll let my friend know, and knowing him, he’ll give Sam a discount. Hell, he’ll probably hand him freebies.”

“That’s really cool, Cas. Thanks. I’ll be sure to mention it to Sam. Although, my brother doesn’t exactly have a sweet tooth. He eats crazy healthy.”

“Trust me. He’ll have issues resisting that place,” he said, smirking.

They had to pause their conversation briefly because of a very dignified old lady who was in need of their assistance. She had stopped at the booth, asking for the toy department. Castiel kindly gave her directions and she thanked them both.

Once she was on her way, Dean, after a short hesitation, asked, “So, um, your family. Do they all live here?”

“Nearly all of them, yes. I don’t want to say that’s why I like taking jobs outside the city, but I’m afraid it does serve as a bonus if I have to leave for a few months.”

“For being a tutor?”

Castiel took a moment before answering. “Not just a tutor. I mean, yes that’s mainly…” He sighed deeply. “I don’t only tutor. I told you I tend to hop around. I take whatever is pretty much available for me, and lately, tutoring was it. The only problem about tutoring though, is that, for obvious reasons, people prefer to have a permanent tutor. But I make a point of not staying for more than a semester at the same place. It’s for emergencies, of sorts. For the time until they find someone else.”

Dean frowned. “Is there a reason for that?”

“That’s not really what I want to do, I suppose. I like doing it, but just—”

“Not enough to keep at it.”

“Yes.”

Reflecting back on their first conversation, Dean asked, “And you really don’t know what you’d like to do?”

Castiel laughed. “That’s the million-dollar question, isn’t it? I don’t know. I thought I knew in my teenage years, but it turned out differently.”

“What was it?”

Castiel bit hard on his lips and lowered his eyes. His arms were crossed over his chest and he shifted on his feet.

_Okay. Bad question, apparently._

When it was clear to Dean that Castiel was not in a sharing mood about this subject, he asked another question.

“What about after the holidays? I’ll continue with my regular schedule at the garage. What about you?”

“Oh, that I never know, I’m afraid. Typically, I have something else lined up for January, but I don’t this year.”

“That doesn’t worry you?”

“It does. More than I’d like to admit. That’s why I was very glad to start working here earlier than planned this year. At least I’ll have a bit more saved. And also—”

His eyes set on Dean, and his smile brightened, nearly making Dean blush on the spot.

“What?”

“I was just thinking,” said Castiel, “that it’s also very fortunate this happened. Otherwise I wouldn’t have been paired up with you. I’m just—I’m happy to be working with you, that’s all. You’re good company.”

Dean’s heart jumped, and even though he wondered if Castiel had truly meant it, or if he was simply trying to lessen the heaviness of the conversation, Dean nonetheless knew where he stood on that part.

“Same.”

And after exchanging long warm stares, they had to go back to work. And even though Dean would have preferred continuing to speak with Castiel, as this was only a too brief account of what he wanted to happen, he was still glad of what he had gotten.

It was slow progress, but progress all the same.

**Notes for the Chapter:**

> Thank you for reading! I hope you enjoy the story so far! I can't believe I have managed to do this for a week already. *fingers crossed that it continues that way*
> 
> (thank you to Danica and Landrala!!!!)


	8. Chapter Eight: Troublesome Times

As the Sunday afternoon carried on, Dean grew determined to get over himself and ask Castiel the real questions.

Since speaking to Castiel after their shift hadn’t worked out well on the day before, Dean was tempted to do so during work.

A time when Castiel would be sure to not magically teleport.

But that approach still bothered him.

_What if he says no and then we have to continue the rest of the afternoon being super awkward?_

_Awesome. I sound like Sammy._

And while Dean struggled with this dilemma for the remaining of his shift, unfortunately the choice ended up being made for him. Not only did customers keep them occupied until the very end, but Dean also learned that he was to meet Rowena in her office immediately afterwards.

Screwing up his plans once more.

To make matters worse, Rowena’s chat hadn’t brought good news either.

Due to his tight schedule, Dean had requested switching his shift of Saturday December twenty-first with someone else. Finishing at five o’clock at _The Milton’s_ gave him an hour to change, quickly clean-up and head to wait wherever Pamela’s events occurred on Saturdays.

It was stressful, but he always made it work.

When Pamela had informed him that the location for December twenty-first had been changed to a neighborhood way across town, however, Dean had severely doubted he would be able to pull this one off.

He had questioned Jo and Charlie about it, as they too were working the event. They had suggested that he ask Rowena for help with his schedule.

“That’s what you guys did?” he had asked them. But they had both shook their heads.

“My shift ends at three.”

“Mine too.”

Which had meant they had plenty of time to reach that new location.

Unlike him.

But he had done as they had advised him to do, and Rowena, being a kindhearted and resourceful manager, had promised Dean that she would do her best to help him out.

But, as previously mentioned, it turned out that she did not have good news for Dean on that front.

Given that Dean was also extremely restricted with his free time, it had left him with very few options to trade with his co-workers, namely Monday or Tuesday night.

Assuming they were in a position to work his shift.

And very few met that requirement.

Dean felt panic set throughout his chest. If no one could help him, he would have to choose between arriving late at Pamela’s night and calling in sick at _The Milton’s_ on Saturday.

And neither option was acceptable to him.

“Rowena, I—is there anything that can be done? Please. Me finishing even just one hour earlier would help me. I—maybe—” and he couldn’t even finish his sentence.

He loathed begging and having to resort to special treatment. And he already felt like his entire month of December was soaking in it as it was.

Rowena gave him a sympathetic look, and said, “Because of your schedule, I would tell you that your best option would be to ask Alicia or Garth yourself.”

Dean shifted on his feet, glad to know not everything was lost.

“But I must warn you, Dean, I already asked them,” said Rowena, “and they didn’t agree or simply couldn’t due to other engagements. But perhaps you may succeed in convincing them.”

“It’s worth the shot.”

“I thought so too, dear. Let me know if it works out.”

Thus, on the next day, which was Monday, Dean stopped at _The Milton’s_ , desperate to plead his case to Garth and Alicia, whom he knew were manning the booth that night.

But Monday had not been kind to Dean. He had woken up late. The alarm on his phone had not rung. He had barely made it to the garage in time, and while he knew that Bobby, his boss, wouldn’t have skinned him alive for it, as Dean was a model employee, this one wrong seemed to have set the coarse for the rest of his day.

He had had to deal with equipment malfunction, general clumsiness, and for some reason, the radio had been busted. Everything seemed to rattle him.

And by the time he showed up at the store, Dean had a heavy heart and felt miserable and tired.

Not the ideal set of mind for what he was supposed to accomplished there.

But he took a deep breath, ignored the tension in his shoulders, and approached Alicia and Garth working at the booth. Dean suggested helping them with their wrapping for a moment, while he made his case.

It took a lot of convincing. Garth couldn’t because of his second job, and Alicia was already working that Saturday night.

“You want me to stay in this damn booth the whole day?” said Alicia, utterly not impressed.

“Shit. I—I forgot you work on Sat—”

“Yes. It shows.”

“I’m sorry. But I—I really need this. I obviously can’t trade with your Saturday nights, as it’s the—but any Monday or Tuesday night that would work for you? I’d—I—like, anything and I’ll do it.”

Alicia let out a deep sigh. She pondered on his offer for a moment, and said, “I’ll do it.”

Dean leaned back from the counter. “You will?”

“Yeah. I’ll do your afternoon shift of the twenty-first like you want. For my shift on the night of the twenty-third.”

_No kidding. Nobody wants to work on that night._

_Which is a problem because—_

“I’m actually working on that night too,” said Dean, panicking.

“We all are,” added Garth.

“Then, the twenty-fourth,” she said. “That would be even better.”

Dean stopped breathing. “But I—the store closes at five on that day."

"And I work the afternoon shift."

"But I work _until_ five at my other job.”

Alicia lowered her eyes. She took a deep breath and then leaned on the counter. “Look, I really want to help you out. But if you somehow can manage to take that shift, it would be really great for me. My last exam is on the twentieth and my entire schedule is built around my exams. But if I don’t work on the twenty-fourth, it means I could leave at the very latest that morning instead of six, and arrive at my mom’s at a decent hour.”

“Where does your mom live?”

“St. Louis. It’s just over a four hour drive. Plus the weather and holiday traffic stupidity.”

Dean took a deep breath.

 _If someone would have done this for me so I could have seen Sam back in his Stanford days—hell,_ now _—I would have been eternally grateful._

_How the hell can I say no to that?_

“Okay. I—I’m not sure how, but I’ll make it work.”

She blinked. “But you just said—”

“You’re covered. I’ll make something work. I’ll talk to my boss at the garage, pick up the slack or—it doesn’t matter. You’re covered. Tell your mom to expect you for lunch.”

She gave him a firm nod, smiling. “Thank you.”

“You’re welcome. And thank you too. It helps a lot. I’ll let Rowena know.”

Walking away from the booth, Dean let out a deep sigh of relief. This was the not the scenario he had hoped for, but it certainly wasn’t be worst one either.

He knew Bobby would help him no matter what, but Dean thought it best to carefully weigh on his options first, and only suggest an alternative to Bobby when he felt confident enough about it.

But this was good news. His problem was solved. And he ended up doing a favor for someone else too. Win-win.

The only regrettable aspect about all this was that he wouldn’t be able to see Castiel on that Saturday.

But the twenty-first was still well over a week from now. Many things had time to happen by then. Hopefully.

And just as he was cheering himself up with that idea, turning the corner to reach Rowena’s office, he ran smack into someone.

Stumbling, it took him a few moments to realize what had happened. After regaining his footing, he looked in front of him.

“Meg.”

“Watch where you’re going.”

“I was. Sorry.” Annoyed looks were briefly exchanged. Dean cleared his throat and moved forward to continue his path.

“So, enjoying Clarence, are you?”

Dean came to a halt. He bit on his lips.

_Keep walking. Don’t answer back. Pretend you didn’t hear._

But mildly aggravated that his newly acquired good mood was slipping away once more, Dean stubbornly turned around.

“What do you mean?”

She lifted an eyebrow. And a cunning smile appeared on her face. “Oh. You haven’t yet? Did he say no?” She stepped forward, scanning him head to feet. “Probably for the best Dean-o. Clarence is not like the rest of us.”

“Why do you keep calling him Clarence?”

Her smile widened. “And what? Call him by his real name? That would be boring.”

“Yeah, okay,” he said, frowning. “See you, I have to—”

“I’m surprised at you though,” she continued.

And curiosity got the better of him. “How come?”

“That you would even consider him given…who you are. I hadn’t pegged you to be that type.”

_What the fuck does that mean?_

“Excuse me?”

“Just—if you do happen to get _lucky_ , remember, he’s okay for a bit of fun, but don’t let your heart-eyes go too far. Or Christmas is going to turn rather sour for you.”

Dean clenched his jaw.

_Is that a threat?_

_Or a warning?_

“Is that so?” he said. “And let me guess, here’s the part where you tell me you know this from experience, even though it’s complete crap?”

“You’ll find out soon enough.”

And she turned on her heels and trotted down the hallway without any additional word.

And Dean was officially done with his stupid day.

**Notes for the Chapter:**

> Thank you for reading! Sorry, I'm running a bit late for this one, but here it is!  
> Hope you had a nice weekend!!
> 
> (and thank you Danica and Landrala).


	9. Chapter Nine: The Sweet Spot

“Who cares about what Meg has to say? Dean, why are you listening to any of this crap?”

“I’m not! I just—I was just curious to hear what you thought of it,” he said defensively over the phone.

“Well, there you have it. I think you should forget about this entire conversation and focus on what Cas is telling you. Never mind what she says.”

“But what do you think it means?”

“Dean, for—you said she has a thing for Cas. She’s probably just trying to get under your skin. And you're letting her.”

Sam, walking down the street with his phone to his ear, came to a sudden halt. He took a few steps back, and after a quick glance at the sign of the shop, he pulled on the front door.

Although the place looked like any other bakery and coffee shop at first sight, he had to admit that it conveyed a pleasant vibe. A few wooden tables and a counter were available for people to sit and eat. But there were also large and cozy-looking armchairs resting by a couple of fireplaces, where people could relax and savor their drinks and pastries. The fireplaces were obviously fake ones, and yet, they were very realistic-looking, thought Sam.

“Dean? Are you gonna let this go?” said Sam, joining the short line leading to the counter and eyeing the display of desserts.

Dean sighed on the other end of the line. “I guess. I’m just…I just—I don’t know why, but now I have the feeling like I’m only going to embarrass myself.”

Sam rolled his eyes. “Oh, we’re there already? I was hoping that for once we’d skip that part.”

“What do you mean?”

“The part where you are doubting yourself. That you’re convinced that you don’t deserve them because they’re better than you. That’s what Meg’s little speech got you thinking, right?”

Silence.

“Stop thinking that,” said Sam, nearly groaning. “Don’t let this—her—discourage you. I know how you are. Even if you move fast, the moment someone just hints at—just, please, continue with what you wanted to do: ask him out.”

There was a long pause, and then Dean said with a faint voice, “I—you’re right, Sammy. I just—you know…”

“Sam?”

Sam frowned when he realized it hadn’t been Dean calling his name, but someone at the bakery.

A familiar voice.

He lifted his eyes and gasped once he saw who was standing from behind the counter.

“Gabriel.”

“What?” croaked Dean. “What about him? Hello?”

Sam, still holding the phone to his ear, approached the counter and stared at Gabriel, who seemed as stunned as he was to find him there.

“Are you stalking me?” asked Gabriel, adopting a mocking tone.

“No,” said Sam, laughing. “I—this is so weird. I—you work here?”

“In a manner of speaking, yes,” said Gabriel, amused. “I own the place.”

Processing the information, Sam remained silent for a moment.

“Hmm. I wondered if my roommate had spilled the beans about this place, but your confusion suggests otherwise,” said Gabriel.

“Sam? Hello?”

“Just wait a minute,” Sam told Dean and lowered his phone. “Bela didn’t say anything. I—my brother works with a guy named Castiel back in Lawrence, and—long story short, he recommended this place once he learned I lived in Chicago.”

Gabriel nodded, understanding. “You’re Dean’s brother?” he said, beaming. “Cas mentioned to be on the lookout for something sweet coming my way. I just didn’t realize how sweet it would be.”

Sam bit on his lips, holding down a grin, and momentarily looked away, feeling embarrassed. But when he returned his gaze to Gabriel, he couldn’t help but look at Gabriel straight in the eyes.

“Sam? What’s happening? Hello?” Remembering that Dean was still waiting for him on the phone, and that he had apparently been jamming the line to the counter, Sam said to Gabriel, “Can—I’ll finish my call and I’ll—”

Gabriel nodded.

Stepping away from the counter, Sam lifted the phone back to his ear. “Hey, sorry. I’m back.”

“Okay. What was that? What’s happening?”

“I ran into Gabriel again.”

“Shut up. Really? Where to this time?”

“That’s the funny part, Dean. I’m at that bakery. _The Sweet Spot_. The one Cas told you about.”

There was a short pause, and then Dean said, “Are you telling me Gabriel is Cas’s friend?”

“Yes.”

“No freaking way. What? This is—this is—”

“I know. He looks totally surprised too.”

“Just surprised?”

Sam had detected a teasing tone in his brother’s voice.

“Okay, before you—you go _there_ , just—”

“Come on! Seriously, Sam?”

Watching Gabriel, who was conversing amicably with a customer, Sam took a moment to observe him properly.

He harbored a bright smile, which was apparently contagious, as everyone stepping to the counter seemed to suddenly turn cheerful.

He took notice of how a lock of hair fell on his forehead. The form of his strong chin and his sharp jawline.

And then his eyes fell on his shoulders. And arms. And hands. And—

Sam felt his heart race.

_Ah, shit._

“Sam, how many times did you run into him, now? Like, not that I’m such a strong believer in that sort of thing, but I think the freaking universe is trying to tell you something.”

“Dean, I—I don’t know what to do.”

“I think you do.”

Sam remained silent.

Which served as an answer for him.

“Sam, hand him the phone.”

“Wh—what?”

“Give your phone to Gabriel for a sec, I want to talk to him.”

Sam’s eyes widened. “Ha-ha. No.”

“Sam.”

“No,” groaned Sam. “I’m hanging up now.”

“Wait—no! Just do it!”

“Dean, why the hell would I do this? What are you gonna say?”

“I just want to say hi.”

“Sure.”

“I swear.”

“Uh-huh. What else?”

“And…and tell him to ask you out again. I like that he keeps asking you and manages to do it without sounding like a total creep. Which is _quite_ something.”

“And are _you_ _quite_ done?”

“Are you letting me talk to him?”

“No.” Sam shook his head. “This is ridiculous.”

“You’re ridiculous, bitch.”

“Jerk.”

“Look, you already made out with him and you liked it—”

“That’s not exactly how I worded it, Dean.”

“Lies. And before you say that you like Bela more or whatever,” he continued, “you like him too. I know you freaking do. So, what’s the worst that can happen, then?”

Sam bit hard on his lips, thinking of one last excuse.

But none came to mind.

Because Dean was right.

“Put him on the phone.”

“You think I’m handing him my phone after what you just said?”

“You told me to listen to you about Meg. Now, it’s my turn to tell you to listen to me, and I’m telling you to do as I say.”

Sam let out a deep sigh. “Fine. Hold on.”

He stood behind the last customer in line, and a few minutes later, with no one behind him, he finally reached the counter again, facing Gabriel.

“Welcome back,” said Gabriel.

“Hi.” Sam cleared his throat. “Um, this is gonna be super weird, and I am seriously worried about what he’ll say, for my case, not yours, but I got my brother on the line and he wants to talk to you.” Sam lifted his phone and offered it to Gabriel.

Puzzled, Gabriel lifted an eyebrow and stood still. But he then reached out for the phone.

“Hello, Gabriel speaking. Hi, Dean.”

There was a long minute of silence, where Gabriel seemed to be listening attentively, until a smile formed itself on his face. “Is that so?” he said.

Sam shifted on his feet as anxiety spread throughout his chest, thinking of the million embarrassing things Dean was probably telling Gabriel in that moment.

_This was such a mistake._

Gabriel let out a few laughs and glimpsed once or twice in Sam’s direction. “I’ll keep that in mind.” There was a short pause. “And I’ll definitely try my best. It was a pleasure talking with you. I knew Cas had a good feeling about you.” He paused once more. “Of course he does.”

Sam’s heart was beating fast.

“Don’t be so sure,” said Gabriel, looking at Sam. “All right? Yup. Have a nice day too. Bye.”

Gabriel handed Sam his phone back.

“Dean?” Sam said, after putting his phone to his ear, but Dean had already hung up.

He took a deep breath. “What did he say?” he asked Gabriel as he shoved the phone back in his coat pocket.

“Well, big bro sort of gave me the green light to not let you leave here today before you agree to go out with me.”

Sam, laughing, shook his head. “He did, huh?”

“Yup.”

And Gabriel stood still, and did nothing but stare at Sam.

And remained quiet.

Grinning.

And Sam only grew more anxious as his silence continued.

_What is the worst that can happen?_

_That I actually like the guy?_

_I think I can deal with that._

And with this in mind, Sam said, “Are you going to ask me?”

Gabriel’s smile widened. “I don’t know. You have politely declined a number of times already. I feel like if I ask once more, it might be considered harassment.”

“What if I tell you I’ll say yes this time?”

“Hmm. And here I was ready to recite you a sonnet.” Sam chuckled, shaking his head. “But since I now know you’ll already say yes, I feel like it would be over doing it.”

They locked eyes for a second. Gabriel reached for Sam’s hand and brushed it with his thumb.

And Sam felt his smile instantly widen and his heart jump.

“Sam, would you do me the pleasure of sharing a nice evening with me, where I will no doubt be delighted of your company?”

“Did you memorize this or did you just come up with it a second ago?”

“Is it working?”

Sam laughed.

“Yes,” he finally said. “I’d like that very much, Gabriel.”

Gabriel instantly lifted his arms in a sign of victory. “I’m going to be totally honest, I’m two seconds away from jumping on the counter and screaming for joy.”

“You don’t say,” said Sam, laughing and scanning around them, hoping no one was listening to them.

“So when do you suggest we do this?” said Gabriel, absolutely beaming at him.

“Tomorrow works with you?”

“Tomorrow? That soon, huh?” he said, smirking.

“We waited long enough.”

“I agree.” But then, Gabriel leaned his head backwards, shutting his eyes tightly. “Crap. I—as much as it kills me to say this, I can’t tomorrow. The holidays are getting to me,” he said gesturing their surroundings.

“Friday? Saturday?” suggested Sam.

“Friday would be very difficult. I could Saturday…but it would be late, well…later than I’d like anyway.”

“How late?”

“Ten…wait, I could push for nine.”

“That works with me.”

“All right. Where to? Want to go see a movie? Catch a late dinner? Take a hike in the desert?”

Laughing, Sam said, “I like the idea of a dinner and a movie. But can we do this at home?”

“Intimate. I like it. My place or yours?”

“I think my place would be better. I live alone.”

“That’s one hell of an invitation.”

“I meant,” and then Sam started chuckling, realizing how it might have sounded. “I meant—that way it will be just us and not—not—”

“Not with my roommate…who is also your co-worker. Right. I see your point.”

“Is that okay?”

“Sam, it’s more than okay.”

Sam nodded. “Food?”

“I’ll take care of it. I’m the one who asked.”

“But I’m the one who declined way too many times.”

“But you are also providing the location,” Gabriel attested. “And besides, food is kind of my thing,” he said.

Sam opened his mouth, but shut it quickly, admitting that Gabriel had won that argument.

“Any food preferences? Allergies?”

“No allergies.”

“Thai?”

“I love Thai food.”

“Sold,” said Gabriel as he mimicked striking a gavel on the counter. “To the gorgeous man in front of me.”

And Sam felt blood rushing through his cheeks. “You never slow down do you?

“Nope. You better get use to it, because I’m pretty sure the compliments will only increase from this point on.”

“I really don’t see how that’s possible, but okay.”

Sam’s phone buzzed in his pocket. He checked it quickly and sighed.

“I’m sorry. I have to head back. Work is calling.”

“Sad, but understandable. I’m very glad I’ll be able to see you Saturday.”

“Me too. I’m really looking forward to it.”

And they stared at each other for a moment more, until Gabriel said, “Before you leave, and I get your number and address, do I still have time to get you anything _else_ , today?”

“I think we can manage that, yes,” said Sam, grinning.

Gabriel busied himself with filling up not one, but two boxes of sumptuous pastries and chocolates. One, which was meant for Dean, solely contained chocolate, as they both decided he had earned his own box. Sam had given Gabriel his information, and Dean’s so he could send him the box by mail—a service that the bakery offered for less perishable items—knowing it would be a good surprise for his brother.

Sam insisted on paying the full bill, especially Dean’s, despite Gabriel’s protest.

“I was going to give you a discount and freebies anyway because of Cas,” Gabriel reminded him.

It took some convincing, but eventually, Gabriel agreed to let Sam pay for his order if he accepted a discount for Dean’s box at least.

And that he promised to text him before Saturday.

And even stop by the bakery once more if he had the time.

Sam, of course, agreed wholeheartedly.

And as he stepped out of the bakery, he waved Gabriel goodbye through the front window, and was actually disappointed when he realized he had to wait too many days for his liking before their date.

**Notes for the Chapter:**

> Ugh. I'm cutting it close again today lol, but here's chapter nine!! I had fun writing this one lol. *lifting eyebrows*  
> Thank you for reading!
> 
> (and Danica and Landrala, you are the best as always, thank you!)


	10. Chapter Ten: Date Night, Part One

True to his word, Sam had stopped by the bakery once on the Friday morning, just long enough to say hello, and had texted with Gabriel substantially over the days leading up to their date.

Gabriel had continued being his charming self, by making Sam laugh with silly jokes and complimenting him.

But nothing more than that. Almost as if he had been purposely holding back on certain topics—questions and comments—for Saturday night.

And while Sam gathered that it had been a perfectly sensible approach, as they were both incredibly busy, and that he would much rather converse with Gabriel in person anyway, and this on any subject, it nonetheless had done nothing good for his nerves.

Sam hadn’t regretted accepting Gabriel’s invitation. Far from it. The butterflies in his stomach and his increasing merry mood every time he noticed Gabriel had sent him a new message, were, if anything, very telling of that fact.

But he also had doubts. Moments of weakness when worry would creep back into his mind.

Whenever he remembered that Gabriel was still Bela’s roommate.

Whenever he wondered about Gabriel’s expectations. About his _own_ expectations.

Sam reasoned that his tendency to overthink was the culprit for this dubiety and that once Gabriel was standing in front of him, Sam would be free of all this uncertainty.

Yet, it had nonetheless left him extremely anxious.

But after having taken its sweet time, Saturday finally arrived, and as the day progressed, both Sam’s eagerness and trepidation intensified.

Focusing on work had nearly been impossible, and Sam had stared at his phone all day long, checking the time and fearing a last minute cancellation.

But alas, Gabriel showed up at Sam’s door at nine o’clock on the dot, with take out food and a large thermos.

And, of course, tasty treats, which consisted of _Kleinurs, Lussebullars_ and _Kärleksmums_ , that he had baked himself.

Thinking of Sam.

Even though the intention had been to eat while watching a movie, as Sam and Gabriel were unpacking the food, they immediately got lost in a conversation and ended up sharing their meal, laughing and talking to each other, never even leaving the kitchen.

Sam, leaning against the counter, devouring the delicious Pad Tai, listened to Gabriel’s funny story about a very demanding customer he had had on that very afternoon.

Gabriel was eager to hear about Stanford and Dean. In fact, Gabriel had a fair amount of questions about Dean. “I’m asking for a friend,” he said, as they both chuckled.

And Sam asked many questions about how Gabriel got to own a bakery, and listened with fascination about his travels in Europe where he had learned most of his skills.

Warm stares and shy smiles were exchanged between the two, and after a considerable amount of time, they decided that they had consumed enough food to tame their appetite, so they put the rest in the fridge for later, ready to move on to the next part of their evening.

That had been when Sam remembered Gabriel’s thermos.

“What was that for?” he said, pointing at it. “We forgot about it.”

A mischievous smile formed itself on Gabriel’s face.

“I was keeping it for later.”

Intrigued, Sam picked it up. It was large, warm, and of a black color, with a bright yellow _Batman_ logo on it. He untwisted the cap and smelled it. “What is it?”

“I made mulled wine.”

Beaming at him, Sam said, “I’ll get us mugs.”

Thus, not long after, Sam was sitting next to Gabriel on his couch, and as Gabriel poured them each a cup, they began discussing the movie options.

“So, what are we watching?” asked Gabriel, as he handed Sam his mug.

“It’s the holidays.”

“So, a Christmas movie?”

“Too cheesy?”

“I love cheesy. Especially during this time of year,” said Gabriel, smiling at the corner of his mouth. “Are you thinking of one movie in particular?”

“Not really. Why?”

Gabriel was holding down a grin. “May I make a suggestion?”

“Of course. I own a few and we have Netflix. We should be good to track it down.”

“Can we watch your favourite one?”

Sam blinked. “You mean, _my_ favourite Christmas movie?”

“Yeah. Since you suggested this, you must have one.”

Sam stared at him.

“Unless I’m like grossly overstepping some kind of ritual,” said Gabriel. “Like if you always watch it on Christmas Eve or something.”

“No, it’s—you’re not. I’m just—that’s not what I was expecting.”

And without telling him what it was, he stood up, went to his bookshelf and picked up the DVD case of the movie in question. Moments later, after setting it up, he took his seat back next to Gabriel, who had covered his eyes for the element of surprise.

Sam pressed play.

After hearing only a few notes of the opening sequence, Gabriel lowered his hands and stared at the screen, amused. “Wait, that’s your favourite Christmas movie?”

Sam paused the movie. “Yes.”

“ _The Nightmare Before Christmas_?”

“I don’t make the rules,” said Sam. “It is a classic.”

“No argument on that point,” said Gabriel. “But that’s—that’s a Halloween movie. Not a Christmas one.”

Sam slapped his thigh, laughing. “Oh my God. You’re one of those?”

“One of who?” asked Gabriel, smirking.

“People who sees this obvious _Christmas_ movie as a Halloween one.”

“Um, yes. Because it is.”

“But—” Sam shook his head, repositioning himself on the couch. Fully facing Gabriel, he held a serious expression as much as he could. “ _Christmas_ is literally in the freaking title!”

Gabriel laughed at Sam’s mild indignation.

“It’s called _The Nightmare Before Christmas_!” pointed out Sam, half-laughing. “Not _The Nightmare After Halloween_.”

“This is really bothering you, huh?” said Gabriel, trying his best to not laugh.

“It doesn’t bother me, I just don’t get how people don’t see this as a Christmas movie.”

“Can it be both?”

“Well, yeah. It is, sort of. I’m just confused how some people see this foremost as a Halloween movie when the whole plot is about experiencing Christmas.”

Gabriel remained silent, observing him fondly.

“What?”

“Nothing,” he said, still staring at him. He nodded at Sam’s remote. “Let’s get this show on the road.”

And grinning, Sam obliged and they both settled comfortably next to each other.

Although the movie was just over an hour long, it took them more than twice that length of time to finish it.

They constantly paused the movie, often due to laughter. They shared comments about their favourite parts. And Sam learned really early on that Gabriel was apparently unable to restrain himself from singing along. And he was actually quite hilarious at imitating the weird accents.

They also took short breaks for stretching and going to the bathroom. When they realized that they still had the second half of the movie to go through, Sam decided to make popcorn, which they consumed with a few of Gabriel’s treats. They also indulged with refills of the delicious mulled wine.

And they watched the rest of the movie in the same fashion, laughing away.

But this time around, Sam made a point to wrap one arm around Gabriel’s shoulders.

When the credits began rolling, the popcorn bowl and their mugs were empty, and nearly all Gabriel’s treats had been eaten.

Sam and Gabriel had cozily sunk themselves into the couch, their feet rested on the coffee table (with Sam’s feet nearly sticking off the other end of it), and Gabriel’s head was partially resting against Sam’s shoulder.

But nothing more than that.

For now.

“So, what’s your favourite Christmas movie?” Sam asked Gabriel.

Gabriel repositioned himself by sitting up so he could look straight at him. Grinning, he said, “It’s an unconventional choice.”

“How so?”

“Christmas is more like a side story. It’s not about Christmas, it’s more like the story just happens to be set at that time.”

“Oh my God.” Sam snorted at him. “And you were giving me grievance about mine not being a Christmas movie?”

“Well, at least it’s focused on one holiday, not two, so there’s no confusion there,” said Gabriel teasingly, and Sam laughed wholeheartedly, shaking his head.

He then realized Gabriel was staring at him. Not just looking at him, but fully examining him.

“What?”

“I just like the way you laugh.”

Watching him, Sam said, “I like the way you make me laugh.”

They continued exchanging long lingering looks, until Sam said, “So? What is it, then? What’s your favourite Christmas movie? I’m curious now.”

Gabriel opened his mouth, ready to blurt out the answer, but he then shut it quickly, not uttering a sound. A mischievous smile appeared on his face as Gabriel was then inspired by an idea. “Maybe I should let you guess.”

“That might take a while.”

Gabriel put a finger on his own lips, faking deep reflections. “Let’s say I’ll give you three clues and you get three guesses.”

“Good clues?”

“Very good clues.”

Amused, Sam said, “What happens if I win?”

“Oh, you need incentive? Raise the stakes, you say?”

Sam shrugged. “Why not?”

Gabriel paused a moment, and then said, “If I win, I get a second date with you.”

Sam dropped his head, laughing. Unable to contain his smile, he said, “Is that all?”

“Yep.”

Gazing at him, Sam reached out for his hand.

“And what if I win?”

“You get a kiss, of course.”

And it took about everything Sam had to not simply lean in and do that right there and then.

“Are these terms agreeable?” asked Gabriel.

Sam, eyeing Gabriel’s rosy lips, nodded.

“All right. So, like I said. The film occurs during Christmas time, but it’s not exactly a Christmas movie,” he reminded him.

Sam gave him a firm nod, eager for the game to begin.

“First clue,” said Gabriel, repositioning himself on the couch. “It’s part of a franchise.”

“ _Die Hard_ ,” Sam blurted out.

But Gabriel shook his head.

“It falls into the superhero genre.”

Sam shifted his eyes to the left, thinking. “And the whole plot is set during the holidays?”

Gabriel nodded.

Sam repositioned himself as well, once more, reflecting on his clue. He then smiled, and turned to Gabriel. He leaned slowly, and said, “ _Iron Man 3_.”

But he stopped when Gabriel, much to Sam’s astonishment, shook his head again.

Gabriel weighed a long time on his last clue, and then said, “It’s from the nineties.”

Sam frowned.

_Fuck. I have no fucking idea._

_A superhero movie franchise? Sure. There’s plenty._

_But a superhero movie franchise from the nineties?_

_Was it a franchise then? Or did it become one?_

_Hold on. It has to be obvious if he told me these three clues._

_Something that most likely everyone would know._

_Spider-man? No. Not the nine—_

_Super—no._

_And it has to be about Christmas too._

_Shit._

Pondering on the answer, Sam diverted his gaze from Gabriel once more. And that was when his eyes fell on Gabriel’s thermos, on the coffee table.

The thermos with the giant _Batman_ logo on it.

And Sam opened his mouth slightly. He turned his head towards Gabriel. Locking eyes with him, he rested his hand on Gabriel’s chest. And after one final hesitation, he leaned in slowly and stopped inches away from his mouth.

He remained still for as long as he could, and then breathed on Gabriel’s lips, “ _Batman Returns_.”

And without waiting for Gabriel’s confirmation, Sam pressed his mouth on his lips. Feeling Gabriel returning the kiss, and tasting the fruity and acidic taste of the mulled wine, Sam sucked on Gabriel’s bottom lip.

Barely having had the time to savor it, he abruptly broke the kiss, and asked, “It was—that was the answer, right?”

“Yes.”

“Okay. Good, I—” and Sam didn’t care about the rest of his sentence, as he felt Gabriel’s hands gripping on his shirt and pulling him closer.

**Notes for the Chapter:**

> Thank you for reading! I'm glad to see you enjoyed the previous chapter haha and I hope this one was equally enjoyable ;)
> 
> (thanks to Danica and Landrala!!! for all your help and patience lol)


	11. Chapter Eleven: A Solo Night

Shutting the door behind him, Dean threw his keys on his counter and let out the biggest sigh ever.

He was exhausted.

His feet were sore, his back and arms stung, and his whole body was heavy. The moment he stepped into his apartment, all he wanted was to fall into a deep sleep.

And eyeing the kitchen floor, he was convinced that doing so right there and then would be no issue for him.

Overwhelmed with an immense amount of laziness, he made sure his front door was locked, and then simply dragged his feet to his bedroom, leaving a trail of clothes behind him as he went along, only to drop half-naked on his bed, and then, as a last effort, he pulled on his covers and buried himself under them.

The day had been long and his evening had been stressful.

While Pamela’s events from the two previous weeks hadn’t been too much of a hassle, this one had been different. The elite group of the night had been high-level employees from a company called Roman Industry, a company Dean had never heard of before that night, and after that evening, he certainly hoped he would never have to encounter them ever again.

They had been loud, and frankly, demanding. Dean wouldn’t go so far as to call them rude, but it had been clear that a few of the guests had been in dire need of some manners.

_Thank God for Jo and Charlie._

Not that Dean would have lost it on the spot, but he had been on a short fuse for the past couple of days. And that loud—read, obnoxious—ass snapping his fingers at them, openly commenting on the staff while they were standing right next to him, as if they couldn’t understand a word he was saying, and looking at them with an air of superiority, had just about been too much for Dean.

Scenarios of heated discussions and putting that jerk back in his place had certainly filled Dean’s mind for most of the night.

At least the sympathetic looks Jo and Charlie had given Dean had been of tremendous support during the whole night.

But with his mind in a frenzy and feeling fried from his long day, Dean could practically taste the bitterness of the evening in his mouth still.

He let out a loud groan of disgust and snuggled himself even more tightly in his bed covers.

He didn’t want to admit it, but all this pointed to one thing: the load of the holidays was getting to him.

Because of his exhaustion, he had fallen slightly behind schedule at the garage, and even though Bobby had done everything he could to give him some slack, Dean had stubbornly refused to be treated differently.

Thus, in addition to coming to work one hour earlier than usual (to compensate for his tricky schedule of December), he would now also stay another hour on the days he could manage to catch up.

But Bobby, much like Sam, had warned Dean to pace himself.

And though he appreciated the concern, Dean didn’t slow down.

And it was starting to show.

_Come on. Ten more days, and then I can just fucking sleep all day on Christmas. How about that? I won’t even see the day pass so that way I won’t even know it’s depressing. That sounds like a neat alternative right now._

And as he attempted to ease his mind with this idea, Dean also reminded himself that while the first two weeks of December had been rough, he had honestly believed it hadn’t been as demanding as he initially had feared.

_Pretty sure a lot of this has to do with Cas, though._

And here lay the real problem.

Because at this point, Dean was convinced that Castiel was simultaneously a blessing and a curse for him.

On the one hand, Castiel’s presence was a strong comfort for him. A much needed comfort as Dean was beginning to feel the heaviness of his grueling month. The very sight of him was practically restoring Dean’s energy and his good mood on the spot.

As Dean had been dragging his feet over the last week, absolutely done with hearing _Frosty, the Snowman_ to the point of repressing groans every time the song played, Castiel had been jovial and energetic. He even hummed to the Christmas songs, tapping on the counter with his fingers to the beat. Like he actually seemed happy at the sound of them. Of him being at the booth.

He conversed politely with the customers, glad to help, and he also didn’t mind listening to Dean talk about his work, regardless if he understood any of what Dean was referring to or not. He just truly listened to him with attention.

Not out of politeness, but rather because he genuinely wanted to hear what Dean had to say about his day.

And Dean couldn’t remember the last time someone had done this, other than Sam.

And this realization rendered him incredibly nervous.

He had still not asked Castiel on a date, and now, he feared that he had missed his window. With each passing day, Dean’s free time became more and more limited. Until Christmas day, he had perhaps two or three nights of freedom left.

Emphasis on _perhaps_.

And at the rate his month was going, they would soon vanish as well.

Thus, if he didn’t act soon, asking him out or not would no longer be the issue. Having the opportunity to follow through with it would then become the problem.

Which brought in another complication for Dean: it drastically added pressure.

With time fleeting away, his insecurities at play, and his failure to bring himself to utter a few simple words, Dean’s hesitation was only growing.

He was caught in a vicious circle.

And the more time he spent with him, silently or not, the more his feelings for Castiel intensified.

It was precious time he spent observing him. Noticing details. From his mannerisms to the length and shade of his hair. His eyes. And chapped lips.

Every bit of information he learned, small or not, was fascinating to Dean. Every smile, joke, and glimpse was like a gift.

_This is becoming way more than just a crush on some good-looking guy._

_And this is part of the problem._

_Sam’s right._

_I am beginning to think this guy is too good to be true. I already believe it. And soon, I won’t just believe it._

_I’ll know it to be true._

_And once I get there…_

_If I continue down that road before I even get to ask him out, only for this to not work out, this is gonna hurt like a motherfucker._

And yet, fully aware of what needed to be done—and this from the very moment Castiel had stepped into that booth—Dean, fearing the consequences and embarrassment, had stalled.

For the most part, Castiel seemed interested. His warmth and kindness definitely suggested that he, at the very least, liked Dean. He had admitted so himself and there had been moments. Looks. Gentle touches.

But not enough to know for sure.

 _I know he likes me, I just don’t know if he likes me like_ that _. Like I do._

The only light at the end of the tunnel regarding this matter had been Sam’s pep talk following Meg’s encounter, and also, quite unexpectedly, his brief conversation with Gabriel. Although he hadn’t explicitly voiced it, as the topic of discussion had been about Sam, not Castiel, Gabriel had nonetheless implied Castiel’s interest.

And even though Gabriel had no reason to lie, it still remained that this had been Gabriel’s word, not Castiel’s, and Dean simply wished he would get clearer signs from him.

As he thought back on that particular conversation, Dean remembered that today—at this very moment—was the day of Sam’s date with Gabriel.

He smiled and hoped that their night was going smoothly and that Sam hadn’t changed his mind.

_I’ve got a good feeling about this one, Sam. I hope you listened to me._

And with that, since Sam had followed through with Dean’s advice (as far as he knew) and had taken that leap of faith to finally go out with Gabriel despite his stubborn resistance, Dean admitted that it was well time for him to follow through with Sam’s advice as well.

Drunk on exhaustion, this task seemed just as perfectly reasonable as it seemed simultaneously impossible.

Reviewing his schedule in his mind, he concluded that Monday night was his best bet to aim for a date. He wasn’t thrilled that it had to be done at the last minute, as the next day was Sunday, but with him pulling extra hours on the next night at the garage and Castiel working on Tuesdays, Dean’s next night off was the following Sunday.

If it stayed that way, and given everything, there was a strong possibility that it would not be the case.

So Monday night it was.

_At least, because I don’t have time to do anything else, it’s the only item on my to-do list._

And then, he, of course, remembered that on top of his load of laundry that desperately needed tending, and that his fridge needed to be replenished with proper groceries, he also still needed to do his Christmas shopping.

He swore loudly, pulling the covers over his head, in a frustrated manner.

_I don’t know how, but this needs to happen._

_Tomorrow._

_No matter what._

**Notes for the Chapter:**

> Thank you for reading!! Sorry for the intermission of Sam and Gabe's night lol. Part two will be tomorrow and we needed a mini update on Dean (and Cas) lol.  
> Hope you had a nice evening!
> 
> (thanks to Danica and Landrala!!!)


	12. Chapter Twelve: Date Night, Part Two

After losing his shirt, Sam nudged Gabriel onto his lap by tugging on his belt.

Settling themselves into their new position, they gazed at each other, smiling brightly. Gabriel was running his fingers through Sam’s hair as he eyed his torso. He then eased his fingertips down his chest in a lingering manner, enjoying making Sam quiver at his touch.

Sam, feeling his heart pounding, slid his hands slowly inside Gabriel’s shirt, exploring the warm skin of his back, bringing him closer still.

And after smiling at the corner of his mouth, Gabriel leaned in for another kiss, pressing himself against him.

And yes.

Gabriel’s kisses. His soft, lingering kisses. Which also somehow always managed to be executed with strong assertion and in a tender manner.

Just like his touches. Embraces. His everything.

_And it’s driving me nuts._

Gabriel moved his mouth to Sam’s throat, tilting Sam’s head slightly to the right and backwards.

Biting on his swollen lips, Sam tightened his grip on Gabriel’s waist, as he felt tingles on his lower back.

And let out a moan from the back of his throat.

_Okay, he knows what he’s doing._

_Like, I knew that._

_I remembered that._

_But he’s expertly taking his time and —_

_Fuck._

Groaning, Sam, no longer resting his back against the couch, sat up as he delicately pulled Gabriel’s hips towards him, and then lifted his hands to Gabriel’s shoulders for a better hold. Still busying his tongue on his neck, Gabriel let out a laugh at Sam’s readjustment. He leaned his head backwards to get a better look at him.

Running his hands smoothly on his back, Sam inhaled deeply, gawking at Gabriel.

_How in the world did I fall asleep when I went back with him?_

_And why the hell did I wait so long before agreeing to go out with him?_

_I mean, I know that was because of—_

_Of—_

_Shit._

And without meaning to, Sam loosened his grip and diverted his eyes for less than a second.

Hoping his moment of hesitation would remain unnoticed, he immediately locked eyes with Gabriel and leaned in to kiss him again.

But Gabriel did notice and gently stopped him, bringing his fingers to his chin.

“Sam? Everything all right?”

He nodded, smiling warmly at him.

But Gabriel was not convinced.

“Where did you go?” he said, brushing his jaw with his fingertips.

“Just processing.”

Keeping a straight expression, Gabriel asked, “Still hesitating? I know you had doubts about this. But you know, for tonight, I didn’t have any expectations of—”

“No, no hesitation,” said Sam, cutting him off as he shook his head. And then he added, running his hands on Gabriel’s thighs, “Not about this.”

Watching him attentively, Gabriel continued brushing the side of Sam’s face with his thumb. “But something is still bothering you.” He observed him a moment, as if he was weighing on something, and then said, “Does this have anything to do with your—your situation? About this other person?”

Sam bit his lips.

“We never went back to the subject after the theatre but I distinctively remember you saying—”

Sam reached out for his hand. “It’s not that.”

Gabriel stayed quiet.

“Well, yes, it—it is, but not in the way you might think. I—there is an issue, but I feel like it might have evolved into something else. And I—” and the rest of his sentence died in his throat.

After studying him a moment, Gabriel slowly slid himself off of him and sat next to him.

Unfortunately.

But he hadn’t done it with disappointment or annoyance. He still held Sam’s hand.

“Can I ask—I know this is—this is really none of my business…”

“It’s okay. You have a right to ask,” said Sam with a faint voice.

_I really hope you don’t though._

_I know I will have to explain this eventually._

_But I don’t want to do this now._

_Not right away._

Gabriel hesitated briefly, took a deep breath and said, “Can you give me an idea of the situation? I mean…are we talking about an ex? Or an on and off thing? An online admirer?”

“No,” said Sam, letting out a small laugh. He squeezed his hand and shifted closer to him. “No, nothing like that.”

“Okay,” he said earnestly. “I just—I really like you and I just want to have an idea of where you stand in all this.”

“ _This_ is what I want,” he said, squeezing his hand.

_I really, really fucking do._

“And why do I feel like there’s a ‘but’ at the end of that sentence?”

“It’s just complicated. I—and I don’t want to mess this up. Us. _This_.”

“And how do we do that?”

“I don’t know.”

Gabriel sighed. “Okay. We’ll come back to that. But in the meantime,” he said, seriously, “I have another question.”

“Okay.” Sam braced himself. “What is it?”

Gabriel took a deep breath.

“How come you don’t have a Christmas tree?”

Sam laughed. “Is that, like, a diversion or something?”

“I really want to know! I’ve been meaning to ask all night. Not that I’m judging you or anything, but as someone who feels so strongly about Christmas movies, I expected a tree or decorations,” he said, gesturing at the living room.

“I never made a point of setting up anything here as I usually spend the holidays in Lawrence. Dean even waits for me to get there before starting decorating, so…”

“That’s nice.”

Sam nodded, and without meaning to, he then lowered his eyes.

“Not nice?” said Gabriel, puzzled.

“It is. I—” Sam paused and cleared his throat. “With work being intense this year, I won’t be able to go.”

“Oh. I’m sorry,” he said, tugging on his hand.

Sam smiled faintly. “Thanks. It’s okay.” He bit on his lips a moment and cleared his throat once more. “What about you? Do you have any plans for the holidays?”

“Not really. Well—okay, that’s not true. I do have plans. Family is expecting me, and so are many of my friends, but everyone is scattered across the country. And not unlike you, my schedule is a lot, so I always end up making a decision at the last minute.”

“You don’t find this stressful?”

Gabriel took a moment to reflect on the matter. “I never really thought about it, but no. I don’t. I suppose I’m just used to it.”

“So, what I understand,” said Sam, after a short pause, “is that you don’t have anything set in stone for Christmas yet…”

Gabriel smirked. “That is correct.”

“Cool. I mean, it’s, um, interesting information to have.”

Gabriel eased himself closer to Sam. Their faces were inches away, and after letting go of Sam’s hand, he fondled his temple briefly, only to then rest his hand on Sam’s waist.

They remained in that fashion for a long time, until Gabriel took a deep breath and shifted slightly towards him still.

“So, about what we were talking about before…” he whispered.

“Yeah?”

“Since it’s complicated…enough to—I—maybe we should hit the pause button for tonight. Might help with your…processing?”

_That’s not what I want._

_That’s the opposite of what I want._

_Even if I know in the long run it might be for the best._

“Sam, I have zero problem with taking things slow.”

“I might,” said Sam, lifting his eyes to him.

Gabriel laughed. “Is that so?”

Sam nodded.

“What if I promise the wait will be worth while?” he said, lowering his hand even further down.

“This is not helping,” groaned Sam, pulling himself closer. “And it’s confusing.”

“Sorry.” He moved his hand to Sam’s neck. “I was just trying to make a point.”

“Noted.” He gave him a quick kiss and sighed deeply. “I don’t want you to go. But I get it. Fair warning though, if you’re serious about that you better leave now or very soon I won’t let you. And I say this wishing you’d stay.”

“Okay,” Gabriel whispered, and after sucking his bottom lip one more time, he leaned back. They stared at each other for a silent minute, catching their breaths, half-cooling off and half-rethinking their options.

But eventually, Sam and Gabriel were standing in front of Sam’s door, ready to say good night.

Even if neither of them particularly wished to do so.

“When can we do this again?” asked Sam, as Gabriel was putting on his coat. “We are doing this again, right?”

“Yes,” he said, beaming at him. “But I don’t know. We could do something next Saturday for sure, but—”

“That’s too far away.”

“My thoughts exactly. I have to warn you though, my hours are completely insane right now.”

“I know the feeling,” said Sam, upset. “Even when I come back home at a decent hour—and I’m using this term rather loosely, here—I still have work to complete at home.”

“Hmm. I think we are both suffering from the same disease.”

“Seems so, yes.”

They discussed their schedules, hoping to find an evening in the coming week that would work for them both, but it became clear that their safest bet was, unfortunately, the following Saturday.

Unsatisfied with this conclusion, they stood still for a moment, both searching for another option. But none came to mind.

Finally, Gabriel said, “For now, let’s agree to do something on Saturday at least. I’ll continue to text you like we’ve been doing if you want me to,” to which Sam nodded vehemently. 

“And if something changes,” said Sam, “or we feel like we could make something work, we tell the other?”

“Absolutely.”

Sam insisted that Gabriel text him once home so he could know he was safe, and after a long, sweet kiss goodbye, Sam watched Gabriel disappear down the hallway, not believing he was letting him leave.

He shut his door, rested his back against it, and, looking at the ceiling, he exhaled loudly. His overall feeling of the evening left him with jitters across his chest and a giant grin on his face.

_Please, don’t make it so I have to wait until next Saturday to see him._

_And please, make me get a grip next time._

_Because I like him._

_And now I—_

_Please, don’t let me fuck this up._

**Notes for the Chapter:**

> All right! As promised, part two! I hope you enjoyed it :)  
> Thanks for reading and have a nice evening!! I can't believe we're almost half way through!
> 
> (thanks to Danica and Landrala!!)


	13. Chapter Thirteen: An Improvised Invitation

The first few hours of Dean’s Sunday afternoon had been busy, to say the least.

Customers had been waiting in line for the wrapping booth, and unfortunately, some grew impatient and demanding.

So much so, that some (very trusting) people had requested to leave their purchases at the booth so they could continue their errands with the intention of returning to the store later in the day.

With some quick thinking on Castiel’s part, he set up a sheet with everyone’s information and an identification system to make sure no one returned home with the wrong wrapped presents (or none at all).

Dean, smiling at the corner of his mouth as he was busying himself wrapping a Playmobil Victorian-looking house, was impressed by Castiel’s patience and resourcefulness at helping as many people as he could.

He had also been very glad that everyone seemed to at least appreciate Castiel’s effort and had the courtesy to treat him respectfully, despite the fact that some had clearly been mildly aggravated at the situation.

Thankfully, and quite inexplicably, in the last half hour of their shift, things died down somewhat for them. All the presents, those of which had been left behind, had been claimed and no customer had been circling the booth for a little while, thus finally giving Castiel and Dean the chance to catch their breaths and clean up the work stations.

After doing so, Dean sighed deeply and sat on one of the chairs, as he firmly believed he wouldn’t be able to do so for very long.

Castiel, however, after a quick glance around them, verifying that no customer needed their assistance, pulled up a large bag from under the counter, where they usually kept their bottles of water and other personal items, such as their phones.

“What’s this?” asked Dean, amused.

Castiel turned to him, looking slightly evasive as if he had been caught red-handed. “I—I went Christmas shopping last night and I figured I’d do the wrapping here instead of at home since I already have all the equipment at my disposal right here. In the dull moments, of course.” He bit on his lips. “Is it bad to do this during work?” he asked.

“Your secret is safe with me,” said Dean, smirking.

Castiel laughed. “Thank you,” he said and began retrieving items from the bag.

A pair of bright red envelopes. Three rectangular white boxes, which Dean deduced contained shirts. _The nice kind._ A small box, which could have contained anything from a watch to a phone case.

And then Castiel retrieved his final item, a large green and black box.

And that one caught Dean’s attention.

He lifted himself from his seat and joined Castiel’s side to have a better view.

He gasped when he noticed what it was.

_An actual record player._

_A vintage one at that._

“What?” said Castiel.

“Nothing,” said Dean, realizing he had been staring. “It’s just a really nice gift.”

“So, good idea for a present, then?”

“Um, yeah. A record player that’s—”He swallowed hard and the next thing he knew, he blurted out, “Must be for someone special.”

_Shut your mouth, Winchester._

_And please, say no._

“It is.”

Dean’s heart dropped.

_Fuck._

_I knew it._

_Too good to be true._

After studying him for a moment, Castiel shook his head and said, “I meant—” and then he let out a small laugh. As if he had guessed what Dean had been thinking—the same way he always did—he said, amused, “I didn’t mean like for a boyfriend or anyone like that.”

Dean’s eyes instantly locked with Castiel’s, as he momentarily stopped breathing.

“It’s for Gabe,” said Castiel simply. He turned his head, continuing on his task, measuring the ribbons. “He’s been a great help to me this year. I thought he deserved something nice and he always complains about the poor quality of the speakers he has at the bakery. I don’t know,” he said, shrugging. “But I think he’ll like this, no?”

“Um, yeah. This is really cool.”

“Great. I found a couple of records I think he’ll enjoy, too.”

Dean nodded with his eyes bouncing from the box to Castiel.

_Now is the time._

_Do not leave it there._

Dean cleared his throat, and attempting to ignore how his hands were practically shaking, he asked, “And do you have one of those? A boyfriend, I mean. Or a—are you going out with anyone?”

Castiel, seemingly unaffected by Dean’s question, said, “Not at the moment, no.”

Dean nodded, feeling his heart jumping in his chest. “Because you’re…too busy or just don’t feel like it right now?”

“Neither. Just—I guess the right opportunity hasn’t presented itself lately.”

Dean froze on his spot as he held his breath, processing the information.

“What about you?” asked Castiel. His eyes had remained on the task at hand. But he had paused his actions, and his head had slightly turned to Dean, as if he had caught himself at the last moment.

Shifting on his feet, Dean said, desperate to veil the anxiety in his voice, “Same. No one at the moment.”

And then Castiel continued folding the paper.

Dean weighed on his words for a few moments, his heart still pounding. Finally, he drew a quick breath, and said, “But I hope that will change soon.”

“Do you?” said Castiel, smiling. “Are you saying this as a general statement in the hope of meeting someone?”

“No. I—I have someone specific in mind. I mean, I met them already.”

Castiel remained silent.

“But you’re not with them.”

“No.”

“And why’s that? What’s stopped you so far?”

“My flagrant lack of confidence.”

Castiel laughed and turned to him. “I’m having difficulty believing that out of you.”

Dean smirked. “But it’s true.” And then, adopting a mocking expression, he said, “I’m a mess.”

Which made Castiel laugh even more. And he continued staring at him. Intensively. With his piercing blue eyes that rendered Dean weak in the knees.

“So what are you going to do about it?”

“Not sure.” Dean stepped closer. “I guess I’m doomed.”

“It seems so.”

“And you? Anyone in sight?”

“As a matter of fact, I do.”

And after staring at each other for a long time, Dean slid his hand towards Castiel’s, eyeing his lips like they were oxygen. And just as Dean was about to lean in, they both jumped at the announcement over the store’s intercom, reminding the customers that the store was closing in less than fifteen minutes.

They both laughed awkwardly, and Castiel refocused himself on his task, as Dean took a quick step back, crossing his arms over his chest.

_You’re at your freaking job, you idiot._

_A time and a place._

No other customers visited the booth for the remaining time of their shift and Dean helped Castiel wrap his presents quickly. Once they were done, Castiel left a twenty dollar bill in the donation jar and carefully put back his now wrapped present in his bag, while Dean started to clear all the material away.

And then they were left to stare at each other quietly for a few minutes.

Smiling shyly.

And awkwardly.

Castiel leaned on the counter, glancing around the store, watching the last minute customers rushing towards the cash registers.

_Say something._

_Open your mouth and say something._

_You cannot let him leave after what just happened and not say anything._

“Um, Cas?”

“Hmm?” he said, still staring blankly in front of him.

“Cas, are you—do you, um—”

And Dean choked on his question when Castiel turned his eyes on him.

As he waited quietly.

And patiently for Dean to continue.

Looking at him with a deadpan expression.

“Do you—”

_You idiot._

_Fucking say something!_

_ANYTHING._

“Do you—Christmas?”

Castiel frowned.

“Shopping,” Dean added nervously.

“What?”

_WHAT?_

Panicking, Dean said, “With me. I—need to do some Christmas shopping.”

Castiel remained silent for a moment. “And…you want me to…”

“Help me. I’d like you to help me out. If you want. And can. I—yeah.”

_What the actual fuck._

_STOP._

“To do Christmas shopping,” repeated Castiel.

“Yes.”

Castiel studied him a moment. He lowered his eyes, pondering on Dean’s proposal. But when his eyes locked with his, he said, “All right. I can do that.”

Dean swallowed. “Yeah?”

Castiel nodded, smiling.

“Great. I—I know it’s last minute but is tomorrow night fine with you?”

“I can make that work, yes,” he said, grinning warmly at him.

“Awesome.”

And after a quick chat, they agreed to meet at around seven at the corner of Mass and Tulpa Street.

Their shift promptly ended. They said good night.

And Dean kicked himself all the way back to the garage, muttering “Shopping,” under his breath, cursing himself.

**Notes for the Chapter:**

> Thank you for reading! I hope you have a nice weekend!! :D
> 
> (thanks to Danica and Landrala)


	14. Chapter Fourteen: Christmas Shopping

On Monday night, Dean and Castiel met just as planned.

Dean had been a nervous wreck for most of the afternoon, eagerly awaiting his evening with Castiel.

Sure, it hadn’t been the scenario he had hoped for, but after he had mulled it over, he concluded that it wasn’t a lost cause either.

_It’s extra time with him. Alone. Outside of work._

_It’s progress._

_And the evening might start with us shopping, but if everything goes well, it could turn into something else._

_Like what I was hoping for in the first place._

_You know, if I stop fucking up._

He let out a deep sigh.

Dean stood at the corner street where they had agreed to meet, taking in deep, slow breaths, desperate to calm his nerves.

Light snowflakes were falling, slow Christmas music was playing, and while the crowd in the street was marching in a steady beat, the people also appeared to be in a cheery mood. Dean took a moment to observe his surroundings, and with Christmas lights hangings in the trees and front windows of the stores, he had to admit that the scenery before him gave a rustic and pleasant vibe attached to it.

Almost peaceful-like.

Not long after, Castiel arrived, wearing a trench coat and a cozy-looking red scarf. And he was carrying small drinks with him.

“I didn’t know what you liked, so I got us apple ciders,” he said, offering one to Dean.

Stunned, Dean stood still, staring at him.

“They’re small enough so if you don’t like—want—”

“No,” said Dean, urgently. “I do. I do like it. It’s good. Thanks—thank you.” He stepped forward and reached for the beverage. “I was just not expecting that. That’s really nice of you. You didn’t have to do that.”

“I felt like drinking something festive.”

Dean took one whiff and smiled. “It’s actually a good change from the bitter, strong coffee. And you know what? I think with all the holiday work and the Christmas music, I purposely avoided everything that had anything to do with Christmas this month.”

“Including Christmas shopping,” said Castiel, teasing him.

“And festive drinks or food,” he said, smirking. “I think it will be good to remind myself that not everything about this holiday is annoying. Especially since I usually like this time of year.”

“Glad I could be of service then,” he said, beaming at him, as he lifted his cup. “Shall we?”

The street consisted mostly of little local shops, among a few cafés and restaurants. Dean often avoided Mass Street because he always perceived it to be too touristic for his taste.

_And the parking space is terrible._

But he still insisted on visiting the street once a year: for his Christmas shopping. It was a tradition of sorts.

“So, what’s on your shopping list? Who are we getting presents for?” asked Castiel, before taking a sip of his drink.

“My brother Sam,” said Dean, imitating him. Castiel nodded, having expected Dean’s answer. “I’d like to find something for Bobby, my boss. And a couple of my friends. Nothing extensive.”

_And now it sounds like I made it super dramatic for nothing, given I need stuff for, like, four people. Great._

But Castiel didn’t appear to be bothered by Dean’s reply.

“All right,” he said. “You’ll have to let me know a little about them so I can help you. Unless you already have ideas in mind? Were there shops in particular you were planning on stopping by or do you just want to browse?”

_I do already know where to go._

_And I have a pretty good idea of what to search for._

_But then the whole thing will be done in less than an hour._

_And that’s way too short._

“Um, I kinda have ideas, but, um, I fear like I might end up just getting them the same things as last year. I’m trying to think outside the box here. That’s partially why I wanted fresh eyes on this.”

Castiel watched him a moment, and as a smirk grew on his lips, he said, “So, am I to understand that browsing is the option you are choosing?”

“Yeah.”

“Good. It’s the option I was hoping for.”

Castiel suggested that they amble down the street, keeping on one side, and make their way back on the other.

And Dean agreed to his plan wholeheartedly.

As they explored the first few shops, it was a tad awkward between them. They didn’t really know what to say, and mainly focused on discussing the four individuals Dean was shopping for.

Which was better than complete silence, Dean figured.

They skimmed through a store consisting mostly of kitchen appliances, a new age-y store filled with crystals, cozy ottomans and painted glass windows, a music store where Dean eyed with great envy the numerous guitars on the wall, and, of course, a Christmas shop, where Dean and Castiel had a lot of fun perusing the panoply of decorations.

They moved down the street, eventually finished their drinks, and while Dean still hadn’t found any of the items he was looking for, awkwardness had slowly dissipated between them.

At the beginning of the second hour of their evening, they found themselves in a small, yet charming, clothing store. Not really what Dean had intended on shopping for, but he followed Castiel through the store all the same.

Castiel immediately spotted the table displaying colorful, ugly Christmas sweaters and gunned for it with a smile on his face.

They amused themselves for a few minutes examining them more closely.

But then something else caught Castiel’s attention.

He reached the next table over and said, “What about this?”

Letting go of the awful looking sweater he had been holding (which consisted of a pug wearing sunglasses and reindeer ears), Dean looked in Castiel’s direction.

Castiel presented him an item of clothing. It took Dean a few seconds before processing it. And then he burst into laughter.

“What? It’s not that ridiculous,” said Castiel, smiling.

Dean shook his head, waving his hand “No, you don’t get it. I—I already gave these to Sam.”

Castiel let out a short laugh, looking at Dean incredulously. “What?”

“Yup,” said Dean proudly, taking hold of the pair of gold boxers with printed mistletoe. “That was last year’s present. As a joke, but still.”

“And did he get you a pair?”

“I bought one for myself.”

Castiel lifted an eyebrow. “Did you?” A smile appeared at the corner of his mouth. “Exactly like this one?”

Dean shook his head. “Similar enough, but not _this_ one. Of another color.”

Amused, Castiel then shifted his attention to the table and examined more closely the multitude of holiday themed boxers before him.

Dean remained silent and watched him with glee, curious to find out which one he would pick.

After a short consideration, Castiel selected the bright green boxers with small candy canes on the top rim of the underwear.

And the strategically located mistletoe printed at the front.

Of course.

“Are these the ones?”

“Nope.”

Castiel’s expression turned glum.

“What’s with the face?” asked Dean, laughing.

“But these are perfect for you. They match your eyes.”

Dean’s heart made a small jump. They gazed at each other for a moment, and then Dean said, “Sorry. But they aren’t the ones I have.”

“Which ones, then?” asked Castiel. Crossing his arms over his chest and still holding the pair of green boxers, he took a step back to let Dean have better access to the table.

Without hesitation, Dean reached for the correct pair of boxers. The mistletoe was still at the front, but small silhouettes of angels were decorating the top rim of the underwear.

And the boxers were of a bright blue color.

Castiel stared at the pair for a moment, until his eyes met Dean’s.

And they remained in that fashion for a long minute, observing the other.

Even if neither of them had voiced it, Dean was convinced Castiel was thinking the same thing he was.

 _The blue ones match_ your _eyes._

Keeping his stare on Dean, Castiel took a step forward. He shifted his gaze to the underwear for a second, and after his eyes returned to Dean, he said, “I—I don’t know how to say this without….”

And the rest of his sentence died in his throat, as he bit on his lips.

“Without what?”

“Without sounding…inappropriate.”

Dean’s heart was pounding.

“Try me.”

There was a short pause, and then Castiel said, “I’ll need proof.”

Dean stopped breathing. “What?”

“You say you own this _particular_ pair. Which I find interesting. For one specific reason.”

Dean listened with acute attention. _I think so too._

“Okay,” continued Castiel, “maybe for more than one reason, but I—I’d like proof of your claim.”

Dean swallowed. “Is that so?”

“Yes.”

Dean’s mind was racing. “That—that’s a rather bold demand.”

“I know. Which is why I warned you.”

Castiel was not diverting his gaze and his expression remained unreadable.

“I wouldn’t want to give you the wrong impression.”

Still as statues, they simply gawked at each other.

Trying to keep his composure and wishing to not ruin the moment, Dean weighed how to approach the situation.

And that was when something occurred to him.

A large smile manifested itself on his face.

“What if I tell you that I’m actually wearing that particular pair right now.”

Castiel’s eyes instinctively lowered towards Dean’s crotch for a split second, just long enough for him to have betrayed himself, and then, with an effort that Dean was sure had been Herculean, he promptly lifted his eyes upwards.

Dean dropped the underwear he was holding on the table. He glimpsed around quickly to make sure no one was paying too much attention to them, and when he felt satisfied of the conditions, he lifted his shirt, slightly pushed down the edge of his pants, thus revealing the bright blue underwear.

Castiel’s mouth opened. He glanced around in turn, assessing a potential threat, and then returned his attention to Dean, stepping closer to him.

As subtly as he could, Dean pulled his underwear’s waistband upwards, so as to reveal enough of the fabric so Castiel could discern the angels. And the moment he noticed Castiel’s expression change, Dean knew he had succeeded and quickly fixed his clothes and coat.

“Satisfied?” said Dean, amused.

Castiel, unable to keep his eyes off of him, said, “Yes. Although, I’m not sure that’s the word I would use. As I unfortunately didn’t get to see the most interesting part.”

_Jesus._

_Fucking._

_Christ._

“But I stand corrected,” continued Castiel. “The blue ones on you was a good choice.”

He dropped the green pair of boxers on the table and, quite casually, he suggested, “I am suddenly starving. Want to grab something to eat before we continue?”

Dean nodded. “I just have to make a quick purchase first, though.” He seized the green pair of boxers Castiel had been holding.

Castiel lifted an eyebrow. “You want a spare in another color? I told you. The blue ones was a good choice for you.”

“These aren’t for me. They are for a friend. I think he’ll like them.”

Castiel smirked at him. “Will he?”

“I hope so. I think medium should be his size. No?”

“I think it’s a fair bet, yes.”

And both smiling, they made their way to the front of the store to wait in line.

The rest of the night flew by far too quickly for Dean. Just as Castiel had suggested, they headed to the next restaurant they could find, only two doors over, and consumed delicious ramen noodles with beers for the next hour.

During their meal, they laughed and shared a lot of funny familial anecdotes. Dean was happy to learn that Castiel was a music lover as well. And while Castiel considered himself a “music enthusiast,” the more he elaborated on the subject, the more Dean felt like he was quite the connoisseur. They discussed their favourite bands and genres, and soon, once that ice had been broken, the topics of conversations were pouring between them. Favourite shows. Places they had travelled to. Best summer jobs they had had in their youths.

Anything.

And even though none of the subject matter could remotely be considered deep or even intimate, Dean didn’t care. He was having a terrific time.

As the evening progressed, when they eventually continued with their shopping, Dean had caught himself eyeing Castiel’s hand on more than one occasion.

As well as Castiel’s lips.

For starters.

With clear ideas of doing something about it.

But he didn’t.

By the end of the evening, which ended with both of them drinking hot chocolate to keep warm, Dean had succeeded in finding the perfect gift for Sam (a book series about serial killers—ideal to feed his brother’s weird obsession), as well as everyone else on his list (Castiel included).

Dean had had a genuinely nice evening.

One he hadn’t had in a very long time.

And he felt his heart grow heavy when they reached their original meeting spot, signalling the end of their evening.

Castiel quickly inquired where Dean had parked his vehicle, and once he learned it was situated on Lazarus Street, which was a few streets over, _and_ on the same street he had parked his own car, they headed in that direction slowly, side-by-side.

They stopped at the corner of Tulpa and Lazarus Street and after an exchange of shy looks, Castiel informed him that his car was parked down the street to their right.

Which was in the opposite direction of where Dean’s car was.

So they stood still, facing each other on the sidewalk.

“This was great,” said Dean. “Thanks for your help.”

“No problem. I had a great time too. And I’m not coming back empty handed, which is very surprising for me,” he said, lifting his bags.

_Ask him._

_Hug him._

_Kiss him._

_Ask him._

His throat was dry, and with the simple prospect of uttering those words—still, after everything—Dean felt panic spread throughout his chest.

Castiel turned his head, eyeing his side of the road for a second, nearly looking as if he was about to head out.

But he remained grounded in his spot.

“Um, Dean? I meant to ask you something.”

Dean swallowed hard. “What is it?”

Castiel bit his lips, and after a brief contemplation, he said, “I—I have—are you free this Saturday?”

Sure he had misheard him, Dean nonetheless blurted out, “Yes.”

“You are?”

Dean nodded firmly at him, taking a small step forward.

A smile grew on Castiel’s face. “Okay. I—I have to—my family has this holiday gathering. And I—I was wondering if you’d like to come with me.”

_He—a family thing._

_He wants to bring me to—_

_Is this happening?_

_I can’t breathe._

Dean felt his smile creep onto his face.

At Dean’s silence, Castiel continued, “I know it’s probably a lot but—and you know how I feel about them—but—”

“Cas, no. It’s—Saturday sounds—”

And that was when Dean realized what he was saying.

When his heart sank.

And when his face took on a look of horror at the word “Saturday.”

_NO._

_No, no, no—_

_Fuck! No. Please._

“Dean?”

“I—I can’t. I’m so sorry. I—I just remembered I—”

He bit his lips hard, terrified of saying another wrong thing.

_Like the fact that I have a third job. That I don’t have time to have a life. That—SHIT._

And disappointment couldn’t have been more obvious on Castiel’s face.

_And great. Because I’m being super fucking vague, now it looks like I changed my mind after he told me it was at his family’s and it totally looks like I just wanted to—_

_WHY?_

_Why is this bullshit happening?_

_FUCK._

Desperate to rectify the situation as best as he could, Dean said, “Cas, I’m so sorry. I would. Really. I—but like I said…I just remembered that I already have, um, plans.”

_PLANS?_

“It’s all right, Dean,” said Castiel understandingly. “Don’t feel bad. It’s my fault for having waited this long to ask.”

_And with this, I officially ruined everything._

They stayed put for a long minute, not knowing what else to say, until they both snapped out of it when an impatient driver honked at another driver a few feet away from them.

“Well, I, um, I should head home,” said Castiel. “It’s getting late. Long day tomorrow.”

Dean nodded, being at a loss for words.

Castiel gave him a shy smile and said, “I’ll see you Thursday.”

And then he turned around and walked down the road.

And Dean, quite beside himself, did nothing but stare, feeling the pit in his stomach growing, until he began walking to his car.

Sitting in his vehicle, holding the wheel, he looked at the empty spot where Castiel had been standing a minute ago.

And let his head drop on the wheel, wondering what the hell had just happened.

**Notes for the Chapter:**

> Thank you for reading! I hope you enjoyed this update *smirks*  
> Hope you're enjoying your weekend!
> 
> (thanks to Danica and Landrala!!)


	15. Chapter Fifteen: Chocolates and Phone Calls

On Tuesday night, while stuffing his face full of chocolates, Dean, stretching on his couch after a long warm shower, was listening to Sam talk about his date with Gabriel.

Dean had tried calling Sam many times on Sunday, but Sam hadn’t answered his phone.

Which Dean had hoped meant good news, even if, at the time, he had been eager to speak with him.

On Monday, however, it had been Dean’s turn to miss his brother’s calls due to his busy schedule, and given how glum he had felt after his shopping spree with Castiel, he had decided to wait until the following day for an update.

“I don’t understand why you didn’t just explain the situation to Gabe,” said Dean. “Like, you know, ‘So, I used to wanna bone your roommate, but then I met you and I don’t anymore. Because I like you.’ You know? But, like, better than that.”

“ _Better than that?_ " said Sam, exasperated. “Dean, it’s just—you are telling me that it wouldn’t bother you if you were in his position?”

Dean frowned. “No.” Then he took a moment to reflect on Sam’s question some more, and added, “What do you mean?”

“Like, let’s say Benny was still your roommate right now. Hell, he doesn’t even need to be your roommate, but let’s just say that he is for the sake of the argument.”

“Okay,” said Dean, not sure where this was going.

“Would it make you feel uncomfortable to know that Cas has had feelings for him long before he met you? That he still has feelings for him right now, even if he likes you and wants to be with you?”

Silence.

“See! My point! I knew—”

“Hold on,” said Dean, cutting him off. “Just—wait.”

Taking the matter seriously, Dean took a deep breath and truly asked himself this question.

_If Cas revealed to me out of the blue that he had had a massive crush on Benny—or anyone else from my entourage—and this for months, but hadn’t acted it on it, for whatever reason, would that really bother me?_

Dean pursed his lips at the idea.

_That wouldn’t change how I felt about the guy._

_But I would wonder if I was the consolation price. Or just someone Cas was occupying himself with, until Benny—or whoever—became available again._

_And it would definitely be a dark cloud of worries hovering over my head._

_But then again, that’s me. The idiot with self-esteem and trust issues who doesn’t even understand why people want to talk to him in the first place._

_I mean, it already kind of bugs me that something_ might _have happened with Meg._

_And she’s not even my friend. She doesn’t live with me. And Castiel hasn’t said anything about her._

_And yeah. She bugs me._

_Though, that might have to do with her attitude in general._

_And at the end of the day, it still doesn’t mean that Gabriel would react the same way as me._

“The problem is that,” continued Sam, “while I really like Gabriel, and I really do, I—um, the feelings I have for Bela haven’t just…disappeared. There is a clear difference though. Saying that it wasn’t like it was before seems a stupid way to explain it, but it’s true.”

“Okay, I—Sam, I still think you should just tell him though,” said Dean, chewing on another chocolate. “You know you’ll have to eventually anyway, right? And not just because Gabriel deserves to know. I hate to break it to you, but your crush on Bela is not very subtle. You’re borderline hilariously obvious when it comes to your feelings. So, even if you avoid Bela for the rest of your life to not expose yourself, um, one way or another, it will reach Gabriel’s ears. If he doesn’t figure it out himself.”

“I know, I know,” sighed Sam. “And I’m aware that the longer I wait, the more awkward the situation might get. On the other hand, blurting this out in the open, right now, when I’m barely—” Sam stopped talking and sighed loudly. “The point is that I will. Just—we’re taking things slow for now, and as much as I hate to say it, it’s probably the right thing to do.”

Dean let out a grunt. He then helped himself to a spicy piece of chocolate, practically melting in his mouth, making him moan. “Well, all I’m gonna say is that you better get real soon and then marry the guy, because I don’t think I’ll survive without that chocolate now.”

“What choco—wait, you’re—you mean the one I sent you? From Gabriel’s bakery?”

“Yes. And I’m about to die of a magnificent sugary coma. GOD, this is delicious.”

“Dean! You’re eating them?” he yelled, exasperated.

Dean froze with truffles still in his hands just as he was about to take another mouthful. “What am I supposed to do? Look at them? It’s chocolate! The box said ‘For Dean, from Sam.’”

“Yes, because that was supposed to be for Christmas! As in a _Christmas present_ ,” said Sam, laughing, not believing his brother.

Dean eyed the half-empty box, contemplating the idea to put it away and save some for Christmas.

But then he shrugged and decided that chocolate was made to eat, not to look pretty. And picked up another one.

“Did you seriously expect me to not eat it?”

“God.”

Once his laughter had died down, Sam questioned Dean about his progress with Castiel. Not particularly thrilled to discuss this subject matter, Dean nonetheless recounted the events of the past couple of days to his brother with a long sigh.

“Dean, don’t be so hard on yourself. The night might have ended abruptly and differently than you wished, but I don’t see how any of what you just told me was a disaster.”

“Um, I failed to ask him out, _again_ , and then, when _he_ did, I had to turn him down in the most awkward way. And I—this _is_ a disaster!”

“It’s not. I think you should really focus on the fact that Cas asked you out. Wasn’t it what you were constantly doubting? If he liked you or not? You now have the proof that he is indeed interested.”

“I know that, but Sam, I fucked up so bad. I mean, I said I had _plans_ for God’s sake. Like it was some dumbass excuse I came up with once I heard it was a family gathering.”

“Why did you say you had plans by the way?” asked Sam, confused.

“I don’t know! I fucking panicked! I didn’t want the guy to know I have, like, eighteen jobs! That I’m failing at life and struggling to make ends meet and I—”

“Okay, whoaaaaa!” said Sam loudly. He took a deep breath and said, “Dean, put down the chocolate and listen to me for a second.”

Dean groaned and dropped the piece of chocolate he was holding back in the box.

“Like I said before,” said Sam, “don’t be so hard on yourself. Dean, you’re not failing at anything. Far from it. We both know the reason why money is particularly tight for you this year and it’s not your fault. And even if it was! I mean—" Sam let out a deep groan. "It's extremely frustrating for me to watch you struggle, especially when you refuse to let me—or anyone else—help you. And you didn’t _create_ the situation you’re in. And it won’t be like this for long.”

Dean let out a deep sigh.

_I know he’s right._

_But it’s still how I feel._

There was a long pause and then Sam said, “Maybe I—I’m not sure how, but maybe I should check if there would be a way for me to come to Lawrence for Christmas after all. I’d have to let go of some of the cases, and that’s gonna be—”

“Sam, no.”

“But I’m worried! You’re exhausted. All you do is work. Save from yesterday, when was the last time you did something that didn’t involve work? Watched a movie? Took a drive just for the hell of it?”

_I have zero idea._

_Shit._

“And now, this little meltdown?” Sam continued. “You’re fried, Dean. And when this happens you get easily discouraged and you start beating yourself up. In a way that worries me.”

Upsetting his brother had not been Dean’s intention.

“I—I’m sorry.”

“Don’t apologize,” he said, almost laughing. “Just give yourself a break. Okay? And—and as for Cas, Dean, just clarify the situation for him. I have no doubt he will understand, and then simply ask him if another night could work with him. That’s all. Okay? Dean?”

Dean bit on his lips and sank himself into his couch. 

“Dean?”

“Okay. I will.”

“Good. Now, before I let you go back to your snack, do you want me to tell you in what attire Kevin arrived at the firm today? I wasn’t going to say anything, but it’s actually funny and I think you could use a laugh.”

And instantly, a grin manifested itself on Dean’s face.

“Do tell,” he said, fixing his pillow and picking another chocolate.

It would be important to note that while Sam pursued his attempt to cheer Dean up, a _similar_ phone call was occurring between another citizen of Lawrence and one of Chicago.

Gabriel, sipping on his coffee as he took a quick break after having put a few pies into the oven, leaned on the desk of the small office in the back room, next to the kitchen of the bakery, as he was having a conversation with Castiel over the phone.

“What do you think it is? Sam’s situation, I mean,” Castiel asked him.

Gabriel shifted his eyes to the side, pondering on Castiel’s question. “I—it doesn’t matter what it is. As long as Sam knows where he stands…whatever it is, or whatever the outcome, that’s what important now. I just don’t want him to second guess himself.” And then he let out a sigh, repositioned himself, and added, “Okay, well, I realize that technically speaking, in the general sense of things, that’s impossible. For anyone. I just—I don’t want to rush him if it’s only going to confuse him even more.”

“But it looks hopeful?”

“Yes,” he said, smiling warmly. “Like, I’m not taking him for granted, obviously, but I like where this is going.”

“That’s terrific, Gabe. I’m really happy for you.”

“Thanks. What about you? Did you do like I told you? Did you ask your little elf to accompany you at your folks’?”

“Stop calling him that,” said Castiel, aggravated.

“Did you or did you not?”

“Yes.”

Beaming, Gabriel said, “And?” as he took another sip of his coffee.

“He said no. He—he has other plans,” said Castiel in a very grim tone.

“Damn, Cas,” sighed Gabriel. “I know you were looking forward to that possibility. But hey, even if it doesn’t work out this weekend, it doesn’t mean it won’t another time.”

“I don’t think so.”

Gabriel frowned. “What? Why?”

“It’s not simply that he declined, Gabe. It’s the way he said it…it was…I—I was sure—the day before it—and—I don’t get it. I’m a little confused.”

“Um, you and me both. What happened the day before?”

“I did like you said. I let him know I’m single. And interested.”

“Uh-huh? And did you say this as clearly as possible or were you a little vague? Indirect? Like you often are,” said Gabriel, with as much affection as he could.

“I—indirectly…but it was pretty clear. And he was the one who brought up the question, so I thought—maybe I misread it and—”

“I—Cas, wait, I’m gonna stop you right there,” said Gabriel, cutting him off. “There is no freaking way you misinterpreted this. I told you. The guy is into you.”

“And as I said before, how could you possibly know that? Did Sam tell you?”

“Nope,” said Gabriel, happily sipping on his coffee. “Sam didn’t tell me anything.” _Per se_ , he thought. “But I have another source. And it’s a very reliable one.”

“Yeah. Okay,” he said in a sarcastic tone.

“It’s not in your head. Trust your guts.”

“Gabriel, you know, like me, that my instincts about this aren’t the best. I—I’ve made mistakes before.”

Gabriel shut his eyes and leaned his head backwards. “I know, but that was a long time ago.”

He heard Castiel let out a long sigh at the other end of his phone.

“Look, I know how you feel about this,” continued Gabriel. “I know it’s why you’re treading carefully with Dean. You worry about what might happen, but there’s only one way you’re gonna find out.”

“But now I made everything awkward.”

“Maybe. Maybe not. So, he has plans? Okay, this sucks. Especially since I know how tough it must have been for you to invite him, but maybe don’t just go to the dark place right away?”

“But you don’t understand. It’s the way he said it. And now I worry that he—”

“I know what you're going to say, but Castiel, never mind that for now. When are you seeing him next? Is it at work?”

“Yes," he croaked. "On Thursday."

“Great. Then, tell me what you’re going to do about that situation, then?”

“But—”

“No. No buts! What are you going to do?”

There was a short pause and then he said, “You really are insufferable at times, you know that?”

“It’s for your own good,” he said, grinning. “Now speak.”

**Notes for the Chapter:**

> Thank you for reading! I can't believe we're past half-way now!! Almost into the last third.  
> There's still a lot left to happen. Ahem.  
> I hope everyone had a nice weekend!!
> 
> (Thank you Danica and Landrala!!)


	16. Chapter Sixteen: December Twenty-First, Part One

The rest of the week had been agonizing for Dean.

He had been busy spending long hours on his feet, with tension in his shoulders, repressing sighs and grunts.

And being mad at himself.

And despite his promise to Sam, when Thursday arrived, he did not broach the subject of Monday night with Castiel. In fact, besides shy smiles and short nods of acknowledgement, they barely exchanged a few words with each other.

And such was the case on the Friday night as well.

True, the customers had been highly demanding, and that had left them with no time to share a heart-to-heart.

Frenzy was in the air. The people were loud. And Castiel was standing right next to him, as unreadable as always.

_I don’t know what to do anymore._

_Even if I could speak to him, I wouldn’t know what to say._

_If I tell him about the job now, since it’s not what I said on Monday, it’s gonna look like I came up with an excuse._

_And it already looks like I came up with a dumb excuse as it is._

_And every time I open my goddamn mouth, I make everything worse._

And with this sad thought occupying Dean’s mind, Friday night ended, an awkward “Good night” was said, and they went their separate ways.

As for Saturday, since Alicia was covering his shift at _The Milton’s_ , Dean took advantage to spend his day working at the garage.

And while working on cars was far more therapeutic than assessing the wall of weirdness building itself in-between him and Castiel at the booth, his thoughts still circled back to him.

But in the early evening, he tried to Castiel out of his mind, and after a quick stop at his place where he showered and gobbled down some leftovers, Dean found himself across town, in one of the nicest neighborhoods.

He followed Pamela’s directive and instructions (on where to park and where to present himself), and on his arrival, he noticed how unusually anxious Pamela seemed to be and so, immediately offered his help.

Dean was surprised to learn that, in addition to his usual uniform—which consisted simply of a (nice) black shirt and pants, with a red bowtie—he also had to wear a white shawl collar dinner jacket and gloves.

Confused, Dean looked at her.

“This is two seconds away from being a penguin suit, Pam.”

“This is a very nice evening, Dean. And it means that we all have to suck it up in the clothing department,” she said, pointing at herself.

She opened her thick coat to reveal that she was wearing an overpriced shiny grey gown.

With stilettos.

The complete opposite of her typical black boots, jeans and band t-shirt attire. And yet, Dean thought she looked beautiful.

Despite her annoyed expression.

He took a deep breath and added on the other layers as he was told.

It turned out that Dean was not the only one displeased about the dress code. Jo, for one, might not have uttered one comment on the matter, but it was written all over her face. Like Dean, she felt ridiculous.

Charlie, on the other hand, found it amusing. But Dean concluded that it was mostly due to Charlie’s good nature.

Although the waiting staff was to simply circulate the room, carrying drinks and _hors d'oeuvres_ , Pamela reminded everyone that if a guest desired a specific drink, they were to oblige their request promptly at the bar, which had been set up on the left side of the room.

And yes, the _room_.

_The house._

There was no point in denying it: this house was stunning. Posh.

_Epic._

Before the guests started arriving, Dean and the others got to admire the room as the final preparations were taken care of.

High and bright ceilings. A wall of windows, displaying a large garden, illuminated by white holiday lights. Paintings larger than life hung on the walls, like in the movies. An intricate chandelier in the center of the room.

And this was just the house, thought Dean.

Adding a few circular tables (for guests not wishing to walk around too much), the massive Christmas tree near the windows, a small orchestra, which was settling itself on the other end of the room next to a shiny piano, and this scene unfolding before Dean could have easily been mistaken for a luxurious ballroom. The kind he always saw in four-star hotel advertisements.

And despite the fact that this very thought rendered him mildly nervous about the night to come, he nonetheless couldn’t help but enjoy the scene for a moment.

Soon enough, however, guests began arriving, and the room filled up quickly during the first hour. And by the end of the second one, because of the considerable number of guests present, and that some were rather energetic and loud, with abrupt movements, Dean had to take special care when moving throughout the room.

This was not the place where he wanted to make a scene or a mistake.

For the most part, people barely acknowledged his existence unless they needed something.

_I much prefer being treated as though I’m invisible than being looked down on._

_Even if people making you feel invisible is just another way of looking down on you._

And even though there were a lot of capricious guests, Dean took comfort in the fact that the evening was moving swiftly.

He kept his mouth shut, smiled (so he would not look depressed or tired), and watched his posture.

And he tried as best he could to not listen too attentively to people’s conversations. This was done out of self-preservation, knowing that, if he heard a distasteful comment about the staff—or about anything that could be qualified as distasteful, really—his expression would, no doubt, betray him.

Obviously, it was impossible for him to not hear anything at all either. But besides the guests’—at times—ostentatious airs, most of their conversations were rather boring, Dean had found.

Talks about their upcoming holidays in whatever third house they owned somewhere in the world. Or about whichever company they had acquired from under their competitor.

The main complaints he heard were actually not about the staff, but—quite surprisingly to Dean—about the other guests of the soirée.

“This is why I hate coming to these things. I swear, if one more person asks me when Father is going to show up…” huffed a woman, taking one glass from Dean’s tray, without even looking at him.

Based on the expressions of his colleagues, they, like Dean, didn’t appear to be in any distress or aggravated.

When Dean had just returned from the kitchen with a filled tray, he tried to make his way towards the Christmas tree, where a lady had lifted her empty glass to him.

On his way there, however, the entire room suddenly turned its attention to the orchestra when the piano had joined in on “Have Yourself a Merry Little Christmas.”

The whole room hushed to listen properly to the melody.

Which Dean had to admit was beautifully executed.

He offered the woman her drink, and when no one else among her small group seemed to be in need of one, Dean turned to continue his task.

And then, his eyes fell on the orchestra and he stopped dead, nearly dropping his tray.

Castiel was the one playing at the piano with the orchestra.

And playing amazingly well too.

_It sounds like him._

Which had been an odd thing to think considering Dean had been unaware of Castiel’s ability to play piano in the first place.

And yet, listening to the melody, the jovial and peppy tone of the piano, it was undeniable.

And there was something else. Undertones. A few lingering notes, like a hint of sorrow. But briefly enough, as if he was concealing it. Reminding himself that he had to sound happy.

Just like at the store when he appeared to be guarded.

It was him.

And it was perfect.

And all Dean could do was stare, frozen on his spot, with his mouth wide open.

He finally snapped out of it once everyone started applauding at the end of the song.

Castiel stood up from the bench, giving a shy bow as a thank you to the crowd. He was wearing a gorgeous, dark blue, three-pieces tuxedo, and Dean was convinced he was about to faint at the sight of him.

_Okay, so I guess he made other plans too._

_Which makes me feel a little better._

And then, Dean swallowed hard as his mind turned to other details.

_He plays piano like a rock star._

_And what he's wearing should definitely be considered for his wedding day._

_And I'm here, carrying trays in this...outfit._

Dean was overwhelmed by a strong desire to flee the scene. But he remained on his spot all the same.

Castiel began walking to the right, but a woman, wearing an elegant black gown, signaled him to remain where he was and reached his side.

The crowd’s applause died, and she said, “Good evening! Welcome. I know most of you are expecting my brother, but as always, he likes to do a dramatic entrance.” Laughs filled the room. “And as he has _yet_ to arrive to his own party, I will speak on his behalf for now. As you know, we love celebrating this holiday and it means a great deal to us that so many of you were inclined to share it with us. Thank you, for granting us your presence tonight.”

Applause echoed around the room.

“But if you allow me this one indulgence, I have to say that I am particularly grateful this year, because all my brother’s children were finally able to attend tonight,” she said, pointing at a small group of four near the tree, and then turned to Castiel, “including his youngest, and my favourite nephew, who’s been particularly _elusive_ for this event these past few years.”

_Her what?_

Wrapping an arm around Castiel’s shoulders, who seemed absolutely uncomfortable in the spotlight and ready to make a run for it, she then said, raising her glass of bubbly with her other hand, “From the Milton family, Merry Christmas! Happy Holidays!”

And the rest of the room imitated her, while her words resonated through Dean’s skull.

_Milton?_

_Milton like_ The Milton's _?_

_Like—as in—_

_No._

And Dean had stopped breathing, unable to look away from Castiel, confused as ever.

And if Dean was surprised to see Castiel there, that was nothing compared to how stunned Castiel found himself to be once he shifted his eyes and noticed Dean not even a few feet away from him, staring at him.

**Notes for the Chapter:**

> Thank you for reading!! I hope you had a nice day!!
> 
> (Thanks to Danica and Landrala!!


	17. Chapter Seventeen: December Twenty-First, Part Two

Much like his brother, Sam had found Saturday to be slow and uneventful. But as fate would have it, the day would turn out to be holding some surprises for him as well.

Sam’s focus had been terrible, to say the least. And while his work had not suffered during the week, despite the fact that Gabriel had been on his mind, and therefore a major distraction, Sam had failed at keeping his attention on his job.

He had shut himself into one of the empty conference rooms, with his pile of papers, away from everyone’s blabber. And eagerly awaiting his evening with Gabriel, he had constantly checked his phone in case Gabriel had texted him.

Sadly, Sam hadn’t been able to meet with Gabriel throughout the week. Not for lack of trying, though.

With Gabriel unable to wander too far away from the bakery, Sam had attempted to stop by nearly every day. But alas, every time he had tried, by making an early trip before work, making a run for it during lunch hour, and even a detour on his way back home, he nevertheless remained unsuccessful.

Traffic. Delays at work. Additional workload.

Not to mention the state of crisis the firm had found itself in over the week.

But more on that later.

What had complicated the matter greatly, was that Gabriel's hours were chaotic, as he had confessed to Sam. Gabriel, every other day, had to be at the bakery by four in the morning, remain at his shop until the lunch hour was done, when he could finally hurry home to crash for a few hours during the afternoon, only to later _return_ to the bakery for closing hours, and continue working afterwards.

So, yes. _Chaotic._

And once contrasted with Sam’s long hours at the office, with a heavy workload to complete at home as well, it made it impossible for the two to see each other.

His sole comfort, save perhaps his very brief conversation with Dean, had been Gabriel’s daily texts. Which always made him smile.

Gabriel had even left him a hilarious voicemail where he had sung the entire song “What’s this?” from _The Nightmare’s Before Christmas_ , and this, for absolutely no reason at all than just because he had felt like it.

Sam was grinning like an idiot every time he stared at his phone. And because all his co-workers appeared glum or on edge, his cheerful state had generated a lot of curious looks from everyone around him.

But he didn’t care.

His heart was light, the lightest it had been in a very long time, and he owed it all to Gabriel.

And though the week had been long and tiresome, they were finally to meet again, this time at a nice restaurant called _Grimoire_.

For starters.

And his imagination was running wild with it.

And based on his conversations with Gabriel, he wasn’t the only one.

Sam, ready to jump out of his skin, sighed deeply and grabbed his phone.

Sam: I have a confession to make.

Sam: And you’re probably not going to be super impressed with me.

Sam: Since you told me that _Batman Returns_ is your favourite Christmas movie, I’ve had this urge to re-watch it.

Sam: So I did.

Sam: Last night.

Sam: I know!

Sam: I should have waited for you.

Sam: Blame Netflix!

Sam: And a mild insomnia.

Sam: And I was missing you.

Sam: Anyway, what I meant to say here is that I was surprised.

Sam: I know I’ve seen this movie many times when I was a kid and all.

Sam: But MY GOD that was depressing.

Sam: Awesome, of course, but like waaaaay darker than I remembered it to be.

Sam: I thought you said you like cheesy movies this time of year?

Sam: And now, I’m very curious to know why this is your favourite.

Sam: Like you don’t need a reason. But you know.

Sam: Gabe?

Sam: You there?

Sam stared at the screen, hoping for a reply, but nothing.

Sam: And I’m going to stop talking now.

Sam: Because I have sent like a million texts already.

Sam: I’m heading out soon.

Sam: I can’t wait to see you.

Sam put his phone away and reminded himself that he still had quite a few things to take care of before calling it a day.

So he sat up, took another sip of his cold coffee and focused on his work, comforting himself that soon enough, he would be enjoying his evening with Gabriel.

Unfortunately, this was not what happened.

Once he judged that what was left could be tended to quickly in the morning, Sam cleared the room he had been using and brought everything back to his desk (in a very orderly manner), eager to go home.

And he waited for the elevators, carrying his heavy briefcase and computer bag.

And was smiling brightly.

“Winchester, wait up!”

Sam turned around and found Drexel in front of him, panting as though he had run from down the hall.

“Oh, terrific! You’re still here,” he said, out of breath.

“Why? What’s the—”

“Miss Knight needs to talk to you.”

_NO._

_PLEASE, NO._

“Now?”

Drexel frowned at him.

“Yes, NOW. Go!”

The elevator doors opened behind him, and after glimpsing them, Sam asked, “Can it wait? I was just—I have—”

“Look, Winchester, you do whatever you want, but after the stupid apocalyptic week we’ve had here, I suspect that if you don’t show up there right now, after she personally summoned you, there is going to be hell to pay.”

Sam shut his eyes tight and exhaled deeply.

_Maybe it won’t be long._

_Like, she wants to check in on my cases. Or—_

_She’s a busy person. I doubt whatever this is about will take long._

_And I don’t have to meet Gabriel until nine._

_There is still plenty of time before that._

He heard the elevator doors close behind him, gave Drexel a nod and rushed to his boss’ office.

Sam had been right on one account.

The chat with his boss turned out to be very short.

But he had been wrong about everything else.

Due to the many crises that had exploded all over the office during that week, a large number of people had been let go, some had even quit, and some had been reassigned to other cases.

Thus, leaving the office in chaos.

So far, Sam had counted his blessings that besides being shorthanded, which had caused the workload to increase somewhat, not much had changed for him.

Until now.

Miss Knight lost no time to inform him that he was to be reassigned to a new case, starting immediately. This was an urgent matter, coming from one of their highest clients, Monroe Styne, who had apparently found himself in deep waters, and Sam was expected to be ready and caught up with every detail by the next morning.

“Everything you may need will soon be waiting for you in the third conference room, the one next to the one you seem to like.”

Sam was at a loss for words, and when Miss Knight realized that he was still standing there, she said, “Is there a problem?”

“Um, no. I—I wasn’t expecting this.”

She lifted an eyebrow. “You should see this as a promotion. Because it is.”

“Yes, I—thank you.”

“Glad we made that clear. Now I suggest you hurry up because you both will have a long night ahead of you.”

“Both?”

“Yes. You’re not the only one who has been reassigned to this case. Miss Talbot is to join you tonight.”

And even though he knew the alternative would not have been better, Sam sincerely regretted not having stepped into that elevator when he had the chance.

**Notes for the Chapter:**

> Thank you for reading!! oouf. That's really last minute, but here it is!!!  
> Hope you had a nice day!!
> 
> (Thank you to Danica and Landrala!)


	18. Chapter Eighteen: December Twenty-First, Part Three

In his old bedroom, Castiel was leaning on the edge of the armchair, staring into space, while twisting his tie in his fingers.

There was a faint knock on his door, reminding him of the time.

“I’ll be there in a moment, thank you,” he said.

He stood up in an unenthusiastically manner and caught sight of himself in the large mirror hanging over his dresser.

Desperate to ignore the cacophony of the crowd coming from downstairs, he took out his phone.

“Hey, Cas,” said Gabriel. “Thinking of jumping out of the window yet? Making a run for it through the kitchen? Let me know, I know all the exit routes.”

Castiel snorted. “I don’t doubt that for a moment. Um, sorry. I didn’t want to bother you. I know you’re at work.” He set the phone on speakerphone, put it on the dresser and began tying his tie.

“It’s okay,” said Gabriel. “I can take five minutes considering what this is about. How is it so far?”

“Don’t know yet. I’m still in my bedroom.”

“Stalling. Bold.”

Castiel let out a groan. “I can’t believe I’m here. I promised myself I wouldn’t do this anymore.”

“I know, cuz. But you knew what would happen, coming home this early in the month. Honestly, I’m impressed you managed to avoid it last year, so…Just—look at it this way: it’s one night. A few hours. And then you’re free. Smile. Nod. Eat one of those cheese puffs for me. Ignore the fam as best you can. Certainly don’t listen to them. Steal a bottle of champagne like the good old days.”

Castiel paused his action and lifted an eyebrow. “Stealing a bottle of champagne had much more novelty back when we were fifteen. Doing so at my age, and _on my own_ , is just sad.”

“Then find someone to steal it with.”

“There is only one person except you that I’d consider doing that with, for different intentions, of course, and that person isn’t here,” he said, looking at the ground.

“Sorry, Cas. I know it sucks. You can—wait, how did everything go with Dean at the store? You were supposed to let me know.”

“I’d rather not get into that just now,” he said, continuing his task.

“Why?” sighed Gabriel. “What happened? Don’t tell me he passed again!”

“No, he did not,” said Castiel, finishing tying his tie. “But that’s because I didn’t ask him. I didn’t get to. It was…It’s like I feared: I made it weird.”

“Weird how?”

“We just don’t talk. Not that we have much time to do so. But even then, I’m not sure he wants to.”

“I don’t believe that. You’re telling me he didn’t speak to you at all today?”

Castiel pursed his lips.

“Actually, um, Dean wasn’t working at the store today.”

A fact that had pained Castiel to solely learn about it on his arrival at the booth that afternoon.

And realized that it was Alicia who was waiting for him. Not Dean.

And when he had questioned her about it, she had simply shrugged and said that it had been Dean’s idea to switch shifts.

“For the rest—until when?” he had said, trying to not sound alarmed.

“Just today. He had something to do.”

_Okay. That was what he told me, after all. That he had plans._

And even though he knew very well that Dean didn’t owe him any explanations concerning his personal schedule, Castiel couldn’t help but feel hurt and worried that he had failed to mention it to him.

_Don’t read too much into this. Don’t think he did this because of you. And him not telling you doesn’t mean he doesn’t care._

He swallowed hard.

_Even if that’s what I can’t help thinking._

“What do you mean he wasn’t at the store? Aren’t—”

“Gabe, I—I really don’t want to talk about this,” he said, cutting him off. “What about you and Sam? Tonight is your date, right?”

There was a pregnant pause. Castiel expected Gabriel to protest his attempt to change the topic, but he was relieved when Gabriel let it go and answered his question. “Yup. That’s tonight. Finally! Dinner at a nice restaurant. I made a reservation at _Grimoire_.”

“That is a nice restaurant. That’s great.”

“Yeah. Though, not as nice as _Enochian_. Which is the one I really wanted to go to, but…”

“Um, unless you’re planning on proposing, I feel like _Enochian_ would be a tad over-the-top. Not to mention that—” but Castiel stopped mid-sentence when his phone buzzed. He picked it up and let out a deep sigh. “Sorry, Gabe. I have to go. I’m being summoned.”

“And so it begins. Who’s having a meltdown?”

“Your mother,” said Castiel, reading his aunt’s text message. “Which reminds me, she has been nagging me about you. I think she requires proof of life. Just send me a selfie or something and I’ll show it to her.”

Gabriel groaned.

“You can send it to her yourself if you want,” said Castiel, almost amused. “Or better yet, do you prefer calling her?”

“Ugh. I see your point. I’ll send you one.” And then he added with a playful tone, “Should I take one where I’m holding today’s paper like a hostage situation? Or too much?”

“Well, the theatrics would be a clear indication that it isn’t fake,” he said, chuckling. “Take one with discernable Christmas decorations in the background and you should be good.”

Castiel fixed his tie one last time and grabbed his jacket.

“All right. And you do the same. Take one of yourself and send it to me.”

Castiel frowned. “Why would I do that?”

“As much as I hate those evenings, the swag was always the best part.”

“Yeah. I’m not doing that.”

“Please? Come on!”

Castiel rolled his eyes. “Fine. Whatever.”

They said quick goodbyes, Castiel took his picture, sent it to Gabriel, and after one last look in the mirror, sighing, he reluctantly made his way down the stairs.

Standing at the threshold of the room, Castiel kept still and scanned the scene.

While the room was beautifully decorated, some would even say nearly unrecognizable, no amount of decorations could trick his eyes on what he was looking at.

_My nightmare._

He entered the room as subtly as he could, wishing to not attract any attention to himself. He simply nodded and smiled at the people, and then, without meaning to, his eyes fell directly on his aunt Amara, who was heading in his direction.

_Great. Not even five seconds in and I’m already being cornered._

“Castiel,” she said, once she had reached his side. “Good, you’re here, finally.” She fretted over his tie.

“Hello.” He moved her hands away, fixing his tie again.

“Your siblings are by the tree. So are your cousins—well, the ones who are here,” she said, annoyed. “Any word on Gabriel?”

“Yes. Here.” He showed her the picture of Gabriel he had just received. Mischievously grinning, Gabriel was holding a mug next to his face that had “Dear Santa, I tried,” written on it.

“Hmm. Would a phone call have been too much to ask?” said Amara.

“I mentioned it to him, but he said that he was extremely busy. He barely took my call.”

“I see,” she said. “Well, we will have to remedy that _later_. But for now we have to deal with the situation here.”

“Which is?”

“That your father still hasn’t arrived. And your mother…” she sighed.

 _Consider me_ shocked _at this information._

“I guess it’s up to me to salvage this, as always,” she said, looking nervously around.

“All right. Well, I guess I’ll, um, mingle,” he said, trying not to sound so grim.

But Amara stopped him.

“Castiel, wait. I wanted to ask a favour. Since you’re here, do you think you could play us something? It was your father’s idea and we made sure to set up the orchestra next to the piano.”

_God, please, no._

_Not this._

“Like the old times?” she added. “Please? You play so beautifully. What do you think?”

“I—” he swallowed hard, glancing around him, slightly panicking. “I’d rather not, Amara. It’s been years since—”

“Come, now,” she said, smirking. “Anna caught you playing yesterday. We all know you still play—how can you not? You’re so good at it.”

Castiel took a deep breath.

_Not good enough for many, though._

“Playing for myself with no audience—thinking there is no audience—is one thing.”

“Castiel.”

She didn’t need to say more. Her tone hadn’t been firm nor had her eyes been angry.

But Castiel knew that there was no getting out of it at this point.

“One song. That’s it.”

“Wonderful!” She hugged him quickly. “Thank you. Please, after they are done with this song, go introduce yourself to the musicians. They are expecting you. Play anything you want, as long as it’s festive.”

And, soon enough, not quite believing it, Castiel was sitting at the piano. He had half-hoped the music conductor would refuse, despite what Amara had told him, but after a quick introduction with him, he wasn’t so lucky. Disappointed, Castiel simply opted to follow whichever song they had planned next.

“‘Have Yourself a Merry Little Christmas,’” the music conductor said. “Would that be fine with you, Mr. Milton?”

Castiel had to suppress a face of disgust.

_Novak. I prefer Novak._

He nodded to him. “Yes, I know it. Thank you.”

_I had to play it every year._

_At least it won’t be complicated._

“Very well. We’ll let you begin and follow your lead,” he told Castiel, as he handed him the proper music sheets.

And wanting the whole ordeal to be done and over with, Castiel took a deep breath, set the sheets in front of him for good measure, tried to forget how many people were present, and began playing.

Soon the orchestra joined in, and quite surprisingly, he felt a smile grow itself on his face.

Just like it had on the day before.

And though his technique was not what it once had been, nor could it ever be, he was actually enjoying himself.

For a short moment, he felt like his old self again.

And then he played the last note, and just like that, it was over.

And the moment applauses and cheers began, his smile vanished, and he realized how stiff his arms and shoulders were. He held his breath and saluted the orchestra and the crowd.

And once his aunt was done with her speech, Castiel was ready to run for cover.

And then, he saw him.

“Dean.”

“What?” said Amara.

“Nothing.”

For half a crazy second, he believed that by some miracle, Dean had managed to change his plans.

_But I never said where—_

And then he noticed the uniform Dean was wearing.

Stunned, all Castiel could master was to gape at him helplessly. Even when he felt Amara nudge him to his right, Castiel followed her lead with his eyes glued on Dean, processing the information.

_Why didn’t you say—_

_Why did you say you had_ plans _?_

“Helloooo, earth to Cas.”

Castiel jumped at his name and realized he was standing next to his siblings and cousins.

And therefore, lost sight of Dean in the crowd.

“Sorry, Michael. What were you saying?”

“I said that was nice of you to play.”

“Yeah, not bad Cas. You’re a bit rusty, but it almost sounded as good as it used to for a moment,” said Raphael, gulping down his drink.

“Don’t be mean,” protested Anna. “You were brilliant, Cas. As always.”

Castiel nodded as a thank you, while subtly scanning the room for Dean.

“Anna is right. It was just what the evening needed. It’s quite a pity that Gabriel did not grant us his presence,” said Amara. “I ought to have a serious discussion with this boy about what he owes this family.”

“Is that a code for a trip to Chicago to put some senses back in his skull?”

Castiel abruptly returned his focus on the conversation around him.

“About time we did that,” said Michael.

“Gabriel is perfectly fine where he is. Leave him be,” said Castiel.

“Because you say so,” said Naomi. “He’s avoiding the rest of us. I think it warrants a visit.”

_Ah, shit. Now I have to take care of this too now._

But before he could make up an excuse, Anna said loudly, lifting an arm to signal one of the waiters a few feet away from them, “More bubbly over here, please!”

The waiter, hidden behind Michael, hesitated briefly, and then approached them, presenting their tray.

And of course, it was Dean.

Who was looking at everyone but Castiel.

_Fuck. This is bad._

“Castiel, dear,” said Amara, “I thought you mentioned that you were bringing someone? I required everyone to bring a guest.”

_Yes, thank you so much for bringing up this particular topic right the fuck now._

_God, this family._

Dean paused and his eyes turned to Castiel. He then proceeded offering the drinks, as Naomi picked two, handing one to Anna.

“Cas?” said Raphael.

“Sorry. I—I did.” He cleared his throat. “I was going to bring someone. I—unfortunately, they had a prior engagement,” he said, looking Dean straight in the eyes.

“Over this? Hmm,” said Anna. “If that’s not enough to impress them, then I say it’s clear that you shouldn’t bother at all.”

“No, it’s not—I don’t—” Castiel started saying, but his sentence died in his throat.

“Why didn’t you just ask someone else then?” asked Michael. “It’s not that hard, Cas. Literally anyone would do. That’s what I did.”

“Doesn’t mean that’s what I wanted,” hissed Castiel at his brother.

“Children, play nice.”

“Oh, wait. Sir?” Michael asked Dean, who had been quietly stepping away. “Can you bring me a whiskey—actually, make that two,” he said, looking at Castiel. “My brother needs a refreshment.”

“I don’t need re—I’m fine,” said Castiel, panicking.

Dean held his stare for a few seconds, and then turned to Michael and gave him a nod. And moved away from them.

Without a look back at Castiel.

As his family members were continuing their conversation, to which Castiel didn’t listen one word of it, he kept his eyes on Dean, determined to not lose track of him.

After a few minutes, when he judged he had waited long enough, he began walking away from the group.

“Castiel? Where are you going?” said Naomi.

“I—I just need to—”

“Hold on, you barely said anything yet. I wanted to hear more about the store. How is that going?” said Michael.

“Wait,” said Anna. “That’s true? I thought Lucifer was having a laugh at me when he told me this. Last year was one thing but—”

And just as Castiel was convinced more than ever that now was the time to make his exit, Dr. Hess appeared next to Amara, demanding a word.

And with that, Castiel took his chance and walked away.

He spotted Dean waiting by the bar, across the room.

_Dean, why didn’t you just tell me you were working?_

_Why lie?_

_Why—_

_Unless you knew._

_You knew who I was all along._

_No, wait. That’s silly._

_If he knew who I was, then what would have been the point in lying about tonight? Obviously, he would have expected me to be here. Right?_

_His face._

_When he saw me._

_He didn’t know who I was._

_Or is it that he didn’t know I would be here?_

_But I had told him that—_

_SHIT._

Castiel approached the bar slowly. Dean was waiting patiently for the bartender to finish his order.

“Dean?”

He turned his head towards him. “Your drinks will be ready in a moment,” he said. While his tone had been nonchalant, as to not raise any alarms for anyone around them, his eyes were anything but unaffected.

“May I have a word with you?” said Castiel, shifting his eyes towards the hallway, hoping Dean would understand.

“Is there a problem, sir?” asked the bartender.

“No, I—I simply had a question for him. You.”

“Regarding?” said Dean.

_Dean, come on._

“It won’t take long.”

_Please._

“Sorry, I have to go back to work.” Dean filled his tray with the drinks the bartender had rested on the counter. “I hope the evening is to your taste, sir. I’m sorry, I mean, _Mr. Milton_.”

Castiel felt a pang in his chest at the snappiness with which Dean had said the name. He took one step towards him, but Dean stopped him by presenting his tray.

“Your drink.”

Castiel looked at Dean with pleading eyes, but when Dean held his stern stare, Castiel picked up one of the glasses of whiskey, and watched Dean walking as fast as he could away from him.

“Fuck.”

**Notes for the Chapter:**

> Thank you all for reading!! Sorry, I'm running a tad late once again, but here it is!!!
> 
> (thank you to Danica and Landrala!!)


	19. Chapter Nineteen: December Twenty-First, Part Four

Not even ten minutes after Gabriel had hung up with Castiel, his phone rang again. He worried for a second that it was Castiel calling him back, this time reporting his mother’s annoyance at him.

Or worse, the possibility that after cornering him, she had perhaps coerced Castiel into calling Gabriel for her.

Requesting a word.

Something he had been very surprised she had not yet resorted to, since he had made a point of only handing his phone number to a limited few.

And she was not one of them.

But when he noticed it was Sam calling him, he smiled, mentioned to his employee Mirabel that he would be back shortly and went to his office to take the call.

Unfortunately, that call did not bring good news either.

“You’re gonna hate me,” blurted out Sam the moment Gabriel answered by chanting “Greetings, oh handsome one.”

Confused, at first, Gabriel then let out a laugh, remembering Sam’s earlier texts.

“I promise I won’t hold it against you for having watched _Batman Returns_ without me.” And he then added, jokingly, “Just don’t do it again.”

“What? I—oh, that. Right. Shit. Um—”

“Sam, I’m kidding.” He heard him clear his throat. “Sam? What’s wrong?”

“Gabriel, I’m so sorry. I—something came up at work and I can’t leave. I—I have to—I’m so sorry.”

Gabriel shut his eyes and leaned on the desk, biting hard on his lips.

“I was heading out—literally waiting for the stupid elevator,” continued Sam, “and next thing I know, my boss informs me that I have to deal with a brand new case and I’m expected at a meeting first thing tomorrow morning. And now I have a mountain of paperwork to do _and_ read, and it’s—I’m stuck here for the rest of the night.”

“Okay,” said Gabriel. “I—Sam, it’s okay.”

“No, it’s not. Gabriel, I’m so, so, so, sorry. I—short of quitting, I can’t get out of this.” And then, he added, “And I legit considered it.”

Gabriel laughed. “Sam, don’t worry. I get it. Trust me,” he said, looking around him, assessing his own mountain of work, “I get it. I’m just sad I won’t get to see you.” And with his smile widening, he added, “It’s a pity too. I had a _lot_ of plans for tonight.”

Sam groaned. “Now, that’s just cruel.”

And Gabriel started laughing again. “Hey, you snooze, you loose.”

“I’m sorry,” repeated Sam. “I feel awful.”

“Don’t. We’ll just find another time, okay? And it will give me the opportunity to catch up on work and sleep. Maybe that way, it will be easier for us to do something this coming week.”

“Um, this week is Christmas,” Sam reminded him. "Won't it be even more complicated?"

“Right. I—about that—I—” but he stopped his sentence and decided that now was not a good time for this discussion. “Look, I’ll let you go back to work, because you have a lot on your plate right now, and so do I, but I’ll call you back tomorrow, okay?”

There was a short pause, and then, Sam said, “All right. Thank you for understanding. Like, really.”

“It’s no problem. So, that’s it, then? Nothing else to add to this turn of events, your honor?” he said in an over-the-top serious tone.

“I—n—no. That’s it.”

Which gave Gabriel pause.

“Sam?”

“I’m fine. I mean—I’m obviously not fine because the night is ruined, but I—that's it. Nothing else to add.”

Gabriel lifted an eyebrow, but said, “All right, then. I’ll call you tomorrow. And stop feeling bad!”

After hanging up, Gabriel stood still for a long minute, pondering on what to do next.

 _I know I’m the idiot who suggested taking things slow, but prolonging our time_ apart _was not what I had in mind when I said that._

He sighed deeply.

Gabriel, like Sam, had found the week very long. And when they had agreed on setting their next date for the following Saturday, Gabriel had firmly believed that an earlier opportunity would have presented itself during the week.

But despite their constant brainstorming on the matter, and how much they had wished for it, the week had progressed without one, and the next thing Gabriel had known, Saturday had already arrived.

And now, twisting his phone in his hands, Gabriel was tempted with an idea. The same idea which had crept into his mind many times during the week.

_He’ll be there all night._

_Which will give me plenty of time to finish up a bunch of stuff here._

_And then, I could stop by the firm after._

_I don’t want to bother him, though._

_He’s working. And it’s why I never did it before._

_But I really want to see him._

_Even if it’s just for five minutes._

Resolute, Gabriel then put a few freshly baked items, such as some Almond Bear Claws, Chocolate Peppermint Pinwheel cookies, and bagels, in a box to bring to Sam.

Content with his idea, Gabriel then returned to the front of the shop to continue his night.

While the bakery remained busy, with customers coming and going, the rest of the night had not been exhausting, judged Gabriel.

During the last hour before closing, however, Gabriel was granted an unexpected customer.

After serving the said customer a few butter croissants, Gabriel took a moment to observe the man standing in front of him.

“Don’t I know you?” he said, putting the box on the counter.

“Yes. Kipling. _Kip._ We met briefly a couple of weeks ago. The pub on Hound Street. You’re Bela’s roommate.”

“That’s right,” said Gabriel, now remembering. “How did you find this place?”

“Bela. Another of our colleagues was talking to her about needing to find good pastries to bring for Christmas and Bela told her about your bakery. I remembered what she said, and I happened to be in the neighborhood tonight, so I thought to check it out.”

“Cool. Well, thank you for stopping by. And I’ll make sure to thank my roommate for the praise. That was really nice of her.”

“I thought so too. You might have to wait for tomorrow to do that, though. By the way it looked like when I left, her already long night might turn to another _kind_ of long night, if you catch my drift,” said Kipling, smirking.

Knowing full well he should have left it at that, Gabriel nonetheless said, “How so?”

“Well, she’s been reassigned to this major case, you see, and while I’m sure she’s not thrilled about the workload, the company she’s keeping tonight, on the other hand, is definitely another story. And given that she just broke up with her boyfriend, it looked like Winchester is going to be a very nice alternative.”

Gabriel froze on his spot. He said nothing and held his breath.

“And everyone knows,” continued Kipling, “how infatuated the poor guy is with her. For months now, the look on his face every time she shows up, it’s almost sad. But hey, it looks like luck finally turned in his favor, considering how pretty cozy they seemed to be together when I left. And that was a couple of hours ago. When the place was still busy.”

_What is it I always say to Cas?_

_To_ not _go to the dark place?_

_Let’s do that._

_Even if I know that Bela has indeed broken up with Patrick._

_And that I never told her about my date with Sam._

_And that—shit._

He swallowed hard and not able to help himself, Gabriel said, as casually as he could master, “And may I ask how exactly did it looked like?”

“They were sitting side by side, alone in a conference room. Sharing the food they had delivered. Giggling. With smiles and looks. And whispers.”

“Sorry, Gabriel? Sir?”

Gabriel, nearly startled, gave an apologetic nod to Kipling and turned to Mirabel. “What—yes?”

“I was just wondering about the box. The one you left for the pick up orders. There is no tag on it. Who is it for?”

Gabriel held his breath, weighing on his words, and said, in a much more desolate voice than he had planned, “It’s mine. For me…and nobody else.”

**Notes for the Chapter:**

> thank you for reading!! (sorry about yesterday's chapter, it was very late, but here's an early one!!)  
> I know everything looks grim right now, but don't worry, I'm not THAT cruel lol.
> 
> (thank you to Danica and Landrala!!)


	20. Chapter Twenty: December Twenty-First, Part Five

The moment Dean had left Castiel’s side after their brisk chat, he became a walking mess. His whole body trembled. He felt small and stupid. And now he knew why he had always thought Castiel was better than him.

_Because he is, in a way I never imagined._

_And that I actually thought I could be with him is now laughable._

Determined to avoid Castiel for the rest of the evening, Dean kept himself busy. He smiled, even though it was the very last thing he wanted to do. He was eager to help the guests who had tricky orders, thus giving him a break from the room. He circulated with gusto, trying to subdue his desire to flee the place like the plague.

And with great apprehension, he expected another ambush from Castiel at any moment.

To Dean’s surprise (and relief), however, Castiel did no such thing. He never ran into him. Dean’s eyes never found him in the crowd. Even on the numerous accounts when he spotted Castiel’s family.

Castiel was nowhere to be seen.

But Dean knew he was there.

He could feel his stare on him, as though Castiel was following him like a hawk.

Near the end of the evening, Jo appeared next to him, while he was serving a series of Old-fashioned and another drink called Cranberry Cider, which Dean had never heard of. Once everyone had their drinks in hand, Jo tugged him away to where Charlie had been waiting near by.

The girls exchanged worried looks, and Jo said, “Dean, Cas is here.”

“I know.” He fixed some of the drinks left on his tray, as to balance it more properly, and said, “I have to go back.”

“Hold on. Wait—he’s a Milton.”

“Was he spying on us? At the store?”

“Did you know who he really was?”

“No. And of course, not. I—not now,” he said, before storming off, heading towards the center of the room.

This time around, however, he had difficulty quieting down his thoughts. He still did exemplary, as far as he knew, but Jo and Charlie’s quick inquiry brought him an anxious rumination.

And the questions and worries piled up, one after the other in his head.

_Why didn’t he tell me?_

_Why is he working at_ The Milton’s _? It’s not like he needs to._

_Unless he was, indeed, spying on us like Jo suggested._

_Fuck. Everything I said about the store. Complaining about the music. The schedule. The hours. Everything._

_And he—_

_FUCK._

And then, at this moment, Meg’s words echoed in his mind.

“Clarence is not like the rest of us.”

_She fucking knew._

_She must have found out last year when—_

_Is that what he does?_

_Have a fling every year?_

“Don’t let the heart-eyes go too far. Or Christmas is going to turn sour for you.”

_That’s what she said. She literally—_

_I am so fucking stupid._

Quite miraculously, Dean managed to power through until the end of the night without any incident, despite the fact that he was officially done with everyone. He wanted to never have to look at a goddamn tray ever again. He usually helped out the crew with Pamela after gigs, even if he didn’t have to, but on that night, he could not master the will to do so. He handed over his tray, gave his white jacket and gloves to Charlie for her to return to Pamela, and asked her to relay the message that he needed to leave urgently.

Charlie nodded without hesitation, and after thanking her, Dean stormed out. He needed to get out of this place as fast as he could. He had a splitting headache. His entire body was heavy. And he was boiling inside.

But he stopped dead at his car when he found Castiel waiting for him there.

“I thought that was your car. You mentioned the model before and it looked like the one you had vaguely pointed at the other night on Lazarus Street.”

Dean clenched his jaw.

_I am so not in the mood._

“Good for you.” He stepped forward and unlocked his door.

“Dean, I need to explain something.”

“There’s nothing to explain. Everything is actually pretty clear.”

“Dean, please.” He shut Dean’s door before he could step inside. “I’m sorry. I know you might be upset that I didn’t tell you who I was—”

“ _Might?_ ”

“But I—I didn’t want anyone to know and—”

“Why?”

“What?”

“Why didn’t you tell me? Why didn’t you want anyone to know?”

Castiel frowned at him. “Are you—were you not just in there? Would you advertise this?” he said, gesturing behind them.

“What? That you have money? That you are a Milton? That you own _The Milton’s_?”

“I don’t own—”

“Why are you pretending to work there?”

It was as though Dean had slapped him.

“I am not _pretending_ to work there. I _work_ there. With _you_ , remember?”

“Why? It’s obvious you can do without it.” He swallowed hard. “God, I feel like such a fucking idiot.”

“Dean, I wasn’t trying to deceive you. I just—I was going to—why didn’t you tell me about tonight? Why say you had plans?”

“Oh, hell no,” he said, lifting his finger, cutting him off. “Let’s not compare that to—to _that,_ ” he said, pointing at the mansion.

“I wasn’t—” Castiel began saying, but Dean did not let him finish.

“That is _not_ the same thing. Cas, I didn’t tell you about my _third_ job on Monday because I felt embarrassed. Even if I know I shouldn’t complain because some have it even worse, it still makes me feel awful about myself. And I didn’t want to give you the wrong idea about me. Like, I’m—and that was before! But now?” he said, almost laughing. “Imagine how _humiliating_ it is for me now. Not only did you find out about it anyway, and this, in the most embarrassing manner and certainly not because I had chosen to tell you, but now I also have to deal with the fact that you own the goddamn store I work at as well. Where, for weeks, you lied to me about everything. Your name. Your—you must have laughed yourself silly. Tutoring? Was that planned or did you think of the first thing that came into your head? What were you doing there? And what about Monday when you—”

And his throat closed up. He couldn’t say anything else. He had probably said too much for his liking—and would most likely regret it later—but he didn’t care in that moment.

_I just want this to be over._

Castiel stared at him, with his deadpan expression, quietly for a long minute. He then took a step forward, and in a very even voice, he said, “I’m only going to say this once: while I may have lied, and I am truly sorry about that, I only lied about one thing. And it isn’t about what you might think. My name—my actual _legal_ name really is Castiel Novak. I didn’t lie.” He paused a moment, as though he was weighing on adding something on the matter, but then continued to other points. “I do work at _The Milton’s_. And I am a tutor. I do odd jobs. Because, just like I told you, the one thing I actually wanted to do in life—the one thing that—well, it didn’t happen. And not that it changes anything, but the consequences of this are still following me, over a decade later. So, this is what I do, and unlike what you obviously believe, I do need my employment at the store. And while I am aware that I am luckier than most in many areas of my life, I kindly suggest you to not confuse my parents’ situation for mine.”

His voice had not broken, and had remained smooth and clear.

But his eyes had saddened.

“And as for Monday, the reason why I accepted your invitation, I thought it was rather obvious. It’s because I like you. Which was why I had invited you here. As my date. I was planning on telling you about my family, but when you couldn’t attend, I decided to hold that information until after the holidays. I thought if our jobs at the store were behind us, it would lessen the chances of—I didn’t want you—anyone—acting weird and treating me differently. Because, _sometimes,_ people do this when they find out. But evidently, it was the wrong approach and I failed. So, I’m sorry that I disappointed you or offended you in any way. _Humiliating_ , was the word? That was not my intention, so I’ll make sure it never happens again.”

Dean felt his stomach drop.

Castiel took a step back to return to the house, but came to a halt, and faced Dean again. “Oh, and the one thing I _had_ lied about though, that was about last year. I do remember you. I wasn’t at the store for long, but every time I was there, and I saw you and I—I thought you looked nice. Handsome, but not just—you were so great with the kids. Patient. Kind. And I know how it can get because I had done that gig years before. And yet, despite the fact that this was within the last few days before Christmas, when everyone is absolutely fed up with it, as I’m sure you were too, you still didn’t let it show one second. I wasn’t sure if it was because you hadn’t wanted to ruin it for the kids, or because you just had good ethics, but either way, I thought it spoke a lot of your character. I contemplated the idea of talking to you, but since I knew I would leave town just after Christmas, I decided it was probably a bad idea.” He swallowed hard, not diverting his gaze from Dean. “Giving myself incentive to stay was not what I wanted. But I regretted it. Even if—and then I couldn’t believe it when I saw you were there. _At the booth._ I—I thought that was my second chance. Like—but it doesn’t matter. I see that I was wrong on every account here. So, like I said, I’m sorry to have bothered you.”

And then he paused, held his stare for a few seconds, and when Dean didn’t reply, Castiel turned around and gunned for his house.

Dean watched him leave.

Keeping still.

And feeling so numb, he dropped his keys on the ground.

**Notes for the Chapter:**

> All right, last chapter of this dramatic evening. I know it was painful, but the healing is on its way.  
> I hope you had a nice day and wish you all an awesome weekend!!  
> Thank you for reading!!
> 
> (and thanks to Danica and Landrala as always :D)


	21. Chapter Twenty-One: The Milton's

Dean had been stubbornly standing at the same street corner for the last fifteen minutes. The air was cold, and he kept shifting on his feet to keep himself warm, as he stared at _The Milton’s_ across the street.

Delaying the inevitable.

Not wanting to step a foot inside that store one moment earlier than necessary.

Because he knew what was waiting for him inside, and he wanted none of it.

He hadn’t had a single wink of sleep the night before.

He had stayed in bed, staring at the ceiling, all morning.

And he had ignored every call he had received.

Even Sam’s.

When Dean had arrived home from the Milton’s mansion, he took notice that Sam had attempted to reach him a few times, but being too exhausted and confused, he had not called his brother back.

He had, however, and quite surprisingly, left Bobby a voicemail that he would not come into work the next morning, promising he would (doubly) catch up in the evening instead.

And with that, he had turned off his phone, dropped on his bed and just tried to sleep.

But without luck. The evening had destroyed him.

He didn’t know what to think anymore. He was too overwhelmed to think.

And he had passed most of his night replaying everything in his head, overanalyzing everything Castiel had said and done over the past weeks.

And now, standing on that street corner, dreading the afternoon, he was still tormenting himself over every single detail.

His brooding hit pause, however, when he felt his phone buzz in his pocket. Sam was calling him, yet again.

And after Dean still didn’t pick up, against his desire, he dragged his feet to the store, gathering that he could no longer wait.

He accessed the employees’ lounge and got rid of his winter attire, quickly and quietly, and this in a very orderly fashion, without initiating contact with anyone and staring at the ground.

When he reached the booth, Castiel was already present and busy setting up the work stations.

And while Dean had dreaded this moment since the night before, notably because he felt—still—ambivalent about the whole ordeal, caught in a vicious circle of anger, embarrassment and confusion, he had no idea how he would react once Castiel was standing in front of him.

And the moment he heard Castiel’s usual “Hello, Dean,” and felt his heart skip a beat and his jaw clench, he knew.

Anger had gotten the best of him in that moment.

And thus, Dean ignored him.

He took his place next to Castiel, aiding him in his task, as the store was to officially open its doors to the public any minute now.

But he did so without uttering one word to Castiel.

And not even so much as look in his direction.

Even if he was fully aware that his attitude was very childish of him, and that it was in no way fixing the problem, but solely aggravating it, Dean couldn’t help it. He had not recovered from the night before, and until he did so—if he even could—he was convinced that nothing could ever make him get past the fact that Castiel was a Milton, and that he had lied about it.

_I wish I could simply snap my fingers and be okay with it._

_But I can’t._

_I just fucking can’t._

So, he forced himself to smile and began helping customers with intense productivity like he had never done before.

And his frustration with Castiel only increased as the afternoon progressed. While Dean was boiling in his corner and doing everything he could to ignore him, Castiel appeared to be his usual merry self.

Humming along the songs. Speaking amicably to customers. And to Dean as well, regardless of Dean giving him the cold shoulder.

Like there was not a single problem in the world.

As though he hadn’t spent the night tossing and turning, filled with worry of what the next day would bring.

Not worried in the slightest of what had happened.

Unlike Dean.

The most upsetting part concerning this ordeal, however, was that only one glance from Dean would have sufficed to assess that Castiel was in fact not his usual cheery self at all, and that he had spent most of his afternoon looking at Dean with sad eyes at every occasion he had.

So, they worked side-by-side, in silence.

With very few interactions.

Wrapping presents with next to no moment to spare.

But in the third hour, as it often happened, the amount of customers considerably died down.

“Dean?”

After pausing, he continued folding the paper, keeping his eyes in front of him.

Stubbornly not answering back.

“I—if you want to take your break, you can.”

Silence.

“Dean, did you hear what—”

“I heard. I have to finish this. You go ahead.”

But Castiel did not leave his side. He simply helped cleaning up the working station while they were awarded this small respite.

And when Dean had finished his wrapping and had handed over the present to the elderly gentleman, who appeared to be very pleased, Dean sat on one of the chairs, drank water and stared at the ground.

“Dean?”

“I told you, I’m fine.”

“That’s not what I was going to—can you look at me?”

Hearing a distinctive note of pain in Castiel’s voice, Dean hesitated. He eventually turned his head, but he had taken his time. And even though he knew he shouldn’t have, Dean said firmly, “What?”

And he regretted it immediately when Castiel lowered his eyes. After a moment, Castiel returned his gaze on him and said, “So, this is what it’s going to be like now? You’ll just ignore me or be mean?”

Dean held his stern stare.

“I said I was sorry.”

And then, with his anger spilling out of his mouth, Dean said, “But you still lied.”

And without giving Castiel the opportunity to reply, he grabbed his water bottle and walked towards the half-door. “I’ll take my break.”

Storming off away from the booth, Dean rushed through the aisles, with frenzy building inside him.

To make matters worse, he passed by the _Chocolaterie_ , where Meg was setting up the display of small boxes on the counter. And, against his good sense, Dean made a beeline for her.

“You knew.”

She lifted her eyes and appeared to be amused to find him standing in front of her.

“Dean. What’s up?” She picked up one of the mini-boxes of chocolate and said, “Want one? I’m supposed to make sure everyone who passes by gets one of these. Freebies.”

“You knew,” he repeated, ignoring her comment. “You knew who he was all along. Why didn’t you say so?”

“It wasn’t my secret to tell, Dean-o,” she said, smiling at the corner of her mouth.

Dean scoffed at her. “That is such—spare me the fake morality. If you had any, you wouldn’t have said anything at all, instead of vague comments hinting at it. Why did you do that?”

“I thought I was clear. I wanted to warn you. I could see how you were—”

“Why?” he hissed, cutting her off. “Why do you care? How do you know?”

She opened her mouth slightly, as if she was about to speak, but then had a change of heart and closed it.

Which really didn’t help Dean’s temper.

“Why did you do this? Was it—were you like jealous or something? Like you guys went out last year and he didn’t—or—”

He stopped talking, too angry for words. He took a deep breath and glared at her, waiting for an answer.

But Meg remained silent.

Which greatly annoyed him.

She studied him for an instant, tapping her fingers on the counter. She then glanced around, leaned on the counter, and said, lowering her voice, “I knew who Clarence was, but not because I figured it out when I was paired up with him at the _Chocolaterie_ last Christmas. I knew him well before that. Back in high school, I used to go out with one of his brothers. That’s how I know him.”

That was not the answer Dean had expected.

And after pondering on her words, Dean said, “You mean that…everything you said about—what you told me the other day, that was based on you and Cas’s brother.”

_Not Cas and you._

She nodded.

And relief spread in his chest.

And even though Dean sensed that Meg was telling him the truth, something was still bothering him.

“Okay, but—wait,” he said. “On his first day, when Cas told you he wasn’t working with you at the—you acted like—well, you acted like an angry ex.”

Meg rolled her eyes, groaning. “That’s not what this was about. That’s—that’s actually private. And nothing happened. Although, I have to admit, little Clarence’s gotten quite dashing with time.”

Dean was unimpressed at her last comment. He stared at her, frowning, trying to discern a lie.

“Um, I—don’t take this the wrong way, but you’re telling me that your high school sweet-heart was a Milton?”

She let out a laugh. “Hell, no. I’m not delusional enough to think that what we had was that serious. Which worked with me. Commitments aren’t exactly my cup of tea. We had our fun and it ‘ended’ in good terms. I’m still considered a _friend_ of the family and all,” she said, gesturing around them. “Mostly because we both knew what this was. Like I said, I wasn’t delusional. And I wasn’t stupid enough to expect more than that. But I’ve seen up close what happens to those who do. I know how this family is, Dean. They are generous, but to a certain extent. They have…standards. And they are keeping a close watch on each other. And not just about romantic entanglements. And Clarence? No matter how hard he tried, it hasn’t been easy for him when—”

But Meg was cut off when a customer showed up at the counter.

“Time’s up,” she said to Dean. “Here.” She slid one of the mini boxes of chocolates towards him. “They really are delicious,” she said and then focused her attention to the customer’s request.

Confusion was now spreading through him more than ever, and the only benefit he gathered from it was that his anger seemed to have somewhat, finally, subdued.

Somewhat.

But when Dean returned to the booth, unsure how he felt about the new information he had acquired, Castiel didn’t acknowledged Dean.

He didn’t welcome him back or even look at him. He kept himself extremely busy.

He did exactly what Dean had done to him for the first part of the afternoon.

He did what Dean had wanted him to do at the start of their shift.

He ignored him.

And Dean knew that no matter how he felt about it, he had ruined everything.

Once his shift ended, Dean wasted no time and hurried down to the garage.

But not to work. No, he simply got into his car and went home.

Even if he knew he would surely regret it the next day, as he was already behind schedule due to his morning’s negligence.

But he had officially reached his limit.

So, he drove home in a haze, with a thousand questions and sad thoughts swarming around in his skull.

He took off his coat and boots with great effort, let himself fall onto the nearest chair in the kitchen, and buried his face in his hands.

_So, basically, like I thought, this was doomed from the beginning._

_And this, even if I hadn’t fucked up everything._

_And let’s face it…_

_I definitely fucked up everything._

His phone buzzed again. Sam was calling.

And now, another form of guilt spread through his stomach, knowing that he had dodged Sam’s calls since the night before.

Momentarily tempted to let it go to voicemail, Dean concluded that if he didn’t answer the phone, sooner or later, Sam would get really worried.

So, with a deep sigh, Dean answered.

“Hey.”

“Dean?” Sam’s voice was broken and faint. Dean frowned. “Something’s wrong. And—and I don’t know how to fix it.”

**Notes for the Chapter:**

> Hey everyone! Sorry for the slight delay, once again. This was a really close call and I'm very surprised that I managed to pull this together lol. Just letting you know, I'm dealing with deadlines, so I might be a tiny bit late for the next day or so, but I'll do my very best to still be on time :)
> 
> Thank you for reading!!! Hope everyone is having a nice weekend!!
> 
> (thank you to Danica and Landrala!!)


	22. Chapter Twenty-Two: Late Phone Calls Again

“So, the cat is out of the bag, huh?” said Gabriel, as he was locking his shop’s front door.

“And it’s worse than I imagined,” said Castiel at the other end of the phone call. “I don’t know what to do. I knew it would be awkward and—but this is…this is so bad, Gabriel. I apologized. I explained as best I could. I tried speaking with him. But it seems that the only thing I managed to accomplish with all that, is solidifying his hatred for me.”

“Hatred?” said Gabriel, making a face. He let himself fall into one of the cozy armchairs, where a hot cup of tea was waiting for him on the side table beside it. “Cas, come on. I’m sure he doesn’t hate you. Upset with you? Sure. But _hate_ you? That’s a bit much.”

“What else am I supposed to call it? He barely looks at me, and when he does, it’s just to shoot me a look filled with resentment and anger. And I—”

Castiel let out a deep sigh.

“Okay, Cas…listen. I have to admit that, um, this was not the easiest way he could have found out,” to which Castiel snorted. “But, now, I think you should focus on the important part.”

“Which is?”

“That now Dean knows the truth,” said Gabriel, after clearing his throat. “Which was what you wanted. Right?”

There was a long pause, and then Castiel said, “Gabe, I—I’m very tired right now…and I honestly cannot tell if you are telling me this sarcastically or not.”

“I’m being very serious.”

Silence.

“Yes, I—see, I still can’t tell.”

Gabriel let out a small laugh. “Cas, what’s so difficult to grasp?”

“How can that be the important—how can that be good? I—of course, I wanted Dean to know the truth, but not in that context! That’s the whole problem! And that’s the point I’m trying to make!”

“And the fact is that _now_ that’s how he found out.” He paused a moment and took a deep breath. “Cas, I—believe me, I know how much of a pain it is to deal with the fam’s rep, and I’m sure that Dean’s reaction doesn’t seem too comforting right now, but these were really unusual circumstances. Even for our standards. And this is not the first time you’ve dealt with this, and you had time to mull it over. Dean didn’t. He’s…” Gabriel swallowed hard. “He’s still processing. I can’t promise that he’ll turn around. But if you care about him as much as I think you do, without giving up, letting him catch his breath for two seconds might be worth the try since you say everything else failed…I—I don’t know.”

“No,” said Castiel. “You—you’re probably right. I just—I fear that the problem is not just that I omitted my identity. It’s the _identity_ in question that is the problem. And that, well, I can’t change that. And if Dean can’t get past this, then all I’ve been doing so far was only delaying the inevitable. Which…fuck, this is so messed up.”

“I’m sorry, Cas. I really wish it would have turned out better. But just—my advice is to wait and see for now.” And then he added, “Don’t, like, give up, but…you know.”

“I won’t. Thanks. I’ll—I have a lot to think about.”

There was a moment of silence, when Gabriel was sipping on his cup of tea, convinced that Castiel was digesting their conversation.

But to his surprise, that was not what had occupied Castiel’s thoughts at the time.

“Gabe?”

“Hmm?”

“Um, can—I don’t want to pry or anything, and I might just—but…can you tell me what’s wrong with you, now?”

Gabriel froze with his cup in hand.

“I—what makes you say something is wrong?”

“Don’t take this the wrong way, but you are being particularly wise tonight. As if you underwent your own contemplation today. And I know you were probably trying to stay on the Dean topic just now, but, all day long, I was expecting a mountain of texts from you, asking if there had been any sibling related drama last night. And nothing.”

Biting on his lips, Gabriel put down his cup of tea.

“And you haven’t said a word about Sam. Obviously, something _is_ wrong.”

He sank into the armchair, and said, “Damn you and your…observations.” He took a deep breath, and said, “Things got…complicated on my end, too.”

“How so?

Silence.

“Gabe? What happened?”

He sighed deeply. “Last night, Sam had to cancel because of work. Which obviously saddened me, but that was not the problem.”

“Okay,” said Castiel, listening with attention.

“Then, some guy showed up at the bakery. I recognized him. He’s from Sam’s work. We got to talking, and long story short,” Gabriel paused to clear his throat, “um, I learned that Sam’s new case, the one he had to stay at work for, didn’t just involve him working late. It also involved him working late with Bela. Alone. All night.”

“I—what are you saying? That Sam ditched you for Bela? Gabe, I—that doesn’t mean anything.”

“You’re right. And even if I find it curious that Sam didn’t think of mentioning that detail to me, that’s not what bothered me. Kip, the guy who was here telling me all this, then let slip a whole narrative concerning Sam’s eternal infatuation for Bela. A very known fact all over the office, apparently.”

“Wait, you—shit, you mean—Bela is…that’s why Sam…”

“Yeah.” And then, Gabriel paused a moment, weighed on if he should add another detail about the matter or not, but chose to remain quiet, biting in lips hard.

“Okay, but Gabriel, that’s—I know how this looks, but what did Sam say about it? I mean, that’s what this guy said. Who knows if it’s true or not?”

“I agree. I wasn’t thrilled and I—I was pretty sure there was some truth in there, but, like you said, I tried to not panic. Before Kip arrived, I was contemplating stopping by the firm to see Sam. After, I decided that perhaps that was not the best idea. The last thing I wanted to do was show up there like a jealous—I just decided to wait, get Sam’s story in the morning, while I...”

“Um, process?” suggested Castiel, remembering their earlier conversation.

“Yeah.” He shifted on his seat.

“And what did he say when he called you today?”

Gabriel looked down.

“He didn’t get to say anything because I didn’t take his calls.”

“What? But Gabriel—you just said—”

“I know. But…something else happened.”

Castiel let out a deep sigh of exasperation. “And what’s that?”

“I—when Bela arrived late last night, I—I stupidly asked her about her night. And Cas, she’s a terrible liar. She was purposely vague about a lot of things and told me she had gone out with some friends. Despite the mountain of paperwork she had brought home with her. I know she was lying. And there are only two reasons why she would do that. One, everything Kip said is true, and Sam asked Bela to not mention anything about work to me, because he had omitted that detail himself. Or two, everything Kip said is true and something happened between them that prompted Sam to inform Bela about us. Enough to make her awkward about it. I don’t like either of those options. And given how Bela was last night, I’m fairly certain it is the second option. So, no. I wasn’t too keen on taking Sam’s call this afternoon. Nor—”

“Nor what?” said Castiel in a worried tone.

“Nor to talk to him when he showed up at the bakery tonight. I just…I didn’t want to do the stupid thing of saying the wrong thing, so I did the other stupid thing of just—”

“Ignoring him,” croaked Castiel. “So, if I understand correctly, this is not just about him keeping a few details to himself, it’s also about what might have happened. Which you can’t know until you give him the chance to speak with you.”

“Don’t take this the wrong way, but why do I have a feeling that this comment is not entirely about me?” said Gabriel, almost teasingly.

“You started it. And I’m right.”

“So, what now?”

“What now…” 

Meanwhile, still at his kitchen table, Dean was listening to Sam telling him what had happened on the day before.

Notably that he had cancelled his date with Gabriel because of work.

Which had then turned into a long night working at the office.

With Bela.

Which had rendered Dean completely still, fearing the rest of Sam’s tale.

 _If Sam is about to tell me something happened between him and Bela,_ _I’m gonna eat my freaking hand._

Fortunately, that was not what had occurred.

But close.

It turned out that while everyone had kept their hands to themselves, so-to-speak, Bela had nonetheless took the opportunity to let Sam know of her availability. And interest.

“I immediately made it clear to her that it wasn’t the case for me,” said Sam, “and I told her why.”

Dean let his head drop, as he exhaled out of relief.

_Thanks, Sammy. I might not be done with humanity just yet._

Sadly, the tale did not end there.

Sam then informed Dean that, for some unknown reason, Gabriel had seemingly ceased all forms of communications with him. No calls. No texts. No voicemails. Nothing. At first, Sam had simply concluded that Gabriel had been busy, but by nighttime, when he still hadn’t replied to one single text, he feared that it was something else.

Gabriel was avoiding him.

Dean pursed his lips at Sam’s reasoning. “I don’t get why he would do that, though. He didn’t know anything. And even if he did, nothing happened. Right?”

“Yes. That’s what I thought, too. But the fact remains that he was ignoring me. So—”

“Sam, maybe he really was busy,” said Dean.

“You don’t know Gabriel, Dean. By then, I would have heard from him. So, as I was saying, I decided to pay him a visit to see for myself. If anything, the night before proved to me that I needed to explain a few things.”

_Explanations._

_Yeah. There is a lot of that going around._

“And what happened?”

“He appeared to be okay and then the second he noticed me standing there…he—he wasn’t mad, but his face,” Sam sighed. “I—I can’t explain it, but he knows. I—I don’t think he knows every detail, but he knows enough. About Bela. About last night—and now he just—he doesn’t want to talk to me.”

“I still don’t see how, but if that’s the case—” and Dean stopped mid-sentence.

Suddenly aware of what he was about to say.

Aware of what it would mean.

“If that’s the case, what?”

“Look, I—I’m not saying you did something wrong here, but you did not tell the whole truth to Gabriel, either. And if he is indeed mad at you, maybe there is a reason. Not like you deserve—I mean, just—maybe there’s stuff you don’t know, too.”

_Yeah._

_Let’s pretend I’m totally not biased here._

“I know this, Dean. I completely agree with you and I feel awful about it. Which is why I wanted to talk to him. Not to give him excuses, but to explain. And to—I feel like I fucked this up and I need to fix it. But if I can’t talk to him, how am I supposed to do that?”

Dean shut his eyes. He felt his throat tightening.

“Dean?”

“I don’t know how,” he said in a low, desolate voice, without intending to.

A long pause followed, and Dean knew he had exposed himself.

“Dean? Are you okay?”

Silence.

“You didn’t call me back all day.”

_Yeah. And now that I know Gabe didn’t either, I feel even worse about it._

“Dean? What’s wrong?”

And after a moment of hesitation, Dean took a deep breath and told Sam of his miserable evening from the night before. Of his harsh words to Castiel. Of his anger.

And how Castiel had tried to mend things, but Dean had simply shut him down.

Because of his pride.

And stubbornness.

And that he regretted it.

Even if he still couldn’t see how any of this could be fixed.

Like Sam.

“Dean, listen to me. Was there any time— _any time at all_ —when Cas actually insinuated, out loud, that you were inferior to him?”

“No, of course not, but—”

“Did he or did he not invite you to his family gathering? To go _with_ him. As his date.”

“Yes, but—”

“And he was surprised on Saturday to find you there? Like he had no idea?”

“STOP LAWYERING ME RIGHT NOW. HE STILL LIED. _He lied_.”

“And he gave you an explanation—a brief one, perhaps, but still—followed by a heartfelt apology,” continued Sam, ignoring him, “and apologized again today. And you did what?”

Dean sighed loudly. “Aren’t you supposed to be on my side?”

“Oh, I am, Dean. I will always be on your side no matter what. Which is why I’m trying to make you understand that despite how it might look like, I think Cas has always been on yours as well. And I—I know how you are…”

“Oh, yeah?” he said, nearly aggravated. “And how is that?”

“Um, you tend to blow up, like, the second something happens.”

“Well, I think I have a fucking good reason too.”

“And then,” said Sam, clearing his throat, “after a little while, when you’ve had time to sit down and really think about it, you usually come around and see what’s what. When, of course, the circumstances are acceptable.”

And Dean, even though he knew that everything Sam had just said was right, wasn’t ready to hear anything about it.

“Well, I’m still mad.”

“Of course. And you have a right to be. But…can you honestly tell me you’re _just_ mad?”

Silence.

“Dean.”

“No.”

“So,” sighed Sam. “What are we supposed to do now?”

Dean leaned in his chair as he rubbed his hands over his face. “We have to convince Cas and Gabe that we’re not as worthless as we feel?”

Sam snorted. “That’s the spirit.”

Repositioning himself on his seat, Dean realized he had something in his pocket. When he reached for his pocket, he made a face, realizing it was the small chocolate box Meg had given him.

He looked at the ceiling in frustration.

And then, obviously, opened the box and started eating one of the two chocolates inside it.

As a small comfort.

**Notes for the Chapter:**

> Wow. I know I'm a little late, but I'm really surprised I get to post this lol.I hope you enjoy it and that you had a nice weekend!  
> Thank you for reading!!
> 
> (Thank you Danica and Landrala!!)


	23. Chapter Twenty-Three: Christmas Eve, Part One

Unfortunately for Sam, an excruciating amount of work needed to be accomplished before Christmas, even if he, along many of his colleagues, had to show up at the firm on the day in question.

But his stressful schedule had not been Sam’s main worry.

Gabriel had only reached out to Sam on one occasion since the weekend.

One.

One voicemail he had left him on the morning of the twenty-third. And it had been short and direct, very much so like when he had seen him at the bakery on the Sunday.

“I’m sorry I keep missing your call. I’m very busy. I know you are too. I promise I’ll call back when I can. And when I’m ready.”

_And when I’m ready._

A sentence, which had greatly increased the pit in Sam’s stomach every time he thought of it.

Without wanting to sound too desperate or nagging, Sam had nevertheless called and texted him a few times more, but alas, Gabriel had still not returned his calls.

And although he had been tempted by this option, Sam did not make another appearance at the bakery. It was still Gabriel’s place of work and Sam deduced that cornering him there would have been unfair to him.

And with Dean’s long day of work on the twenty-third and his additional afternoon shift at the store on the twenty-fourth (as Dean had explained to him on their Sunday night phone call), Sam hadn’t heard much from him either by Christmas Eve.

Thus, on his way home, he sent his brother a quick text, praying that Dean was not answering because he was back home, safe and napping away.

His much overdue nap.

And despite this hopeful thought, the second Sam stepped into his empty apartment, he was hit with a wave of sorrow.

At the realization that it was, at last, Christmas Eve.

And he had no one to share it with.

Not even by phone.

_I knew this would be hard, but this is ten thousand times worse now._

But determined to not remain grim, he dropped his computer bag on the floor, put on some Christmas music, and started baking gingerbread cookies, as he and Dean typically did on Christmas Eve.

And drank eggnog.

Lots of it.

And so, nibbling on his cookies and sipping eggnog, Sam, not able to help himself, picked up his phone and called Gabriel.

And left him a long voicemail.

“Hey, Gabriel. It’s Sam. I—I know you have a lot on your plate at the bakery and that you asked for some space. I respect that. But I really miss you,” he sighed into the phone. “And I need to talk to you. To tell you that I’m sorry. I’m so sorry that I didn’t tell you from the get go that my whole situation involved Bela. I don’t know what you know or—you must know some things to request—” He paused, swallowing hard. “At first, I reasoned that there was no point in telling you and creating awkwardness if I was never going to see you again. But the thing is that I—”

And Sam suddenly stopped mid-sentence, as he had finally realized something. A smile formed itself at the corner of his mouth, now excited at this thought.

But before he could continue his message, the dial tone cut him off, informing him that his message had been recorded.

And as he was about to call Gabriel to tell him the rest of his message, Sam was then hit with another idea.

A much better idea.

After a quick check, he managed (by some miracle) to order an Uber, and he promptly put the cookies in a container, grabbed his coat and Gabriel’s present (thanks to online shopping), and dashed out the door.

En route to the bakery.

Sam’s heart dropped, however, when he found out that it was closed for the night. Hopeful that Gabriel might still be present, he knocked loudly on the front door for a long time, and even called and texted him to let him know he was at the door.

But nothing. Not one sign of life.

So, with apprehension, Sam went to Gabriel’s place. And although he got a response this time, it wasn’t the one he had hoped for.

Bela opened the door, surprised to find him there. Loud music, cheers and laughter came from the apartment.

“I want to speak to him,” said Sam. Not the most courteous of greetings, thought Sam, but he needed to get to the point and fast.

She frowned. “Sam, I—he’s not here.”

Sam took a step forward and yelled loudly, “GABRIEL!”

“Sam, he’s not here,” she repeated.

“I don’t believe you.”

She sighed and said, “Look for yourself, then.”

And sadly, just as Bela had stated, Gabriel was nowhere to be seen.

“Where is he?”

“He said that he’d be at his bakery all night.”

“But I just came back from there. And the place was empty.”

And once again, a look of surprise spread on Bela’s face.

“Sam, I swear, that’s what he told me.”

And he believed her.

Unfortunately, that did not solve his problem.

“Anywhere else he could be?”

“Tonight?” She paused, taking the time to fully reflect on it. “No. I—he doesn’t really have hang out spots. Besides the bakery.”

_I was afraid of that._

“You’re welcome to stay and wait for him, but I’m pretty sure he meant to stay away for a while.”

Sam nodded, sighing deeply.

“Thanks. But I think, I’m not feeling—I guess I’ll just wait to hear back from him, then.”

She nodded amicably. “If he comes back though, I’ll make sure to tell him you stopped by asking for him. And I’ll tell him to call you,” she assured him.

Sam smiled faintly. “Okay. Thank you.”

And after wishing each other good night (and Merry Christmas), Sam returned home.

Feeling defeated.

And blue.

Once again.

Ambling down his hallway and fetching his keys from his pocket, he was so depressed by the whole ordeal, it took him a moment to realize that someone was waiting at his door.

“I heard your message.”

Sam froze on the spot. Stunned, he felt the containers nearly slipped from his grip.

“Well, part of it,” said Gabriel. He was comfortably leaning on the wall.

A green box wrapped with a bow in hand.

Sam held his breath.

“And, um,” he continued saying, “I was really curious to hear the rest.”

They stared at each other, smiling shyly, yet warmly.

“Running last minute errands?” asked Gabriel, nodding at Sam’s containers.

“Um, no. I went to the bakery. Looking for you. To tell you the rest of my message.”

Gabriel leaned his head slightly backwards. “Huh. Great minds think alike.”

Sam lifted his keys and, pointing at his door, he said, “Wanna come in? I was thinking of making coffee.”

Gabriel nodded, and after Sam unlocked his door, he followed him inside. Sam dropped what he was holding on the coffee table. Glad to see that Gabriel was busying himself by taking off his coat, thus indicating that he was not in a hurry to leave, or on the fence about staying, Sam put the kettle on and set aside already ground coffee beans next to the French press coffee maker.

He then walked slowly to his living room, where Gabriel had been looking at the snow falling through Sam’s window.

And then, they stared at each other awkwardly, not knowing where to begin.

“Sorry for the radio silence,” said Gabriel finally. “I didn’t mean to shut you out. I just…”

“It’s okay. I—I’m just really happy you’re here.”

_Take a deep breath and get the hard part over with._

“Gabriel, I—the thing about Bela, I’m sorry. I—I should have told you. And I—” he let out a deep sigh.

“Yeah, about that,” said Gabriel, clearing his throat. “Um, I have to confess something as well.”

Sam frowned. “What is it?” he asked, trying to not sound too worried.

“I knew. I knew about it.”

“Yeah…” said Sam, now slightly confused. “I—like I said in my message, I gathered that you did when you—”

“No, I mean, I knew. _Before_. Like I knew about her before this weekend,” specified Gabriel. And at Sam’s shocked expression, he then added, “I—okay, I mean, I didn’t know exactly what it entailed—I still don’t—but, on _that_ morning, I knew—or rather suspected—that it was about her.”

And with that, Sam was more confused than ever.

“How? And—” he stopped speaking, biting on his lips.

_Well, I’m not exactly in a position to ask him why he didn’t say so…_

_But why didn’t he say so?_

“You should have seen your face when she walked in on us,” said Gabriel, lowering his eyes. “But I didn’t want to draw the wrong conclusion, and when it was clear you didn’t really want to elaborate on it, I thought it best to not force it. So, I didn’t know for sure and I certainly didn’t know what, and told myself that until you confirmed it yourself, I should just do my best to ignore it and trust that when you said you were interested, you had meant it.”

“I did. I do,” said Sam, his mind racing. “I—but if you already knew about—okay, wait. I—there is still a lot I need to understand here. Like, if you already knew, what changed on Saturday, then,” to which Gabriel attempted to add something, but Sam continued speaking, “and—but before that, I need to be clear about two things.”

Gabriel hesitated a moment and then nodded at him, letting him speak.

“The first thing is that, yes, my complication was about Bela. I liked her and—but _liked_. Past tense. And I didn’t mention her being there on Saturday because I would have had to explain why it was important to mention it and that wasn’t a conversation I wanted to have over the phone. Which brings me to the second thing. And that’s about Saturday.”

And while Gabriel remained perfectly silent, he shifted on his feet, as he crossed his arms over his chest.

Waiting for Sam to continue.

“At some point during the night, Bela and I decided to take a mini break from work. We were just talking and there was this…um, moment…All that happened was that Bela, um, let me know that she was single again.”

Gabriel took a deep breath. “And how subtly was that information shared?”

Sam hesitated a moment, not entirely sure what Gabriel was asking, and then said plainly, “She told me so. Like, she didn’t—and I immediately told her that I was spoken for. By you. And the moment she knew, she dropped it. She didn’t—nothing happened.”

Gabriel lowered his eyes, appearing to be lost in thoughts.

“I get that after everything,” continued Sam, treading carefully, “you might doubt me, but I swear that’s what happened. I would never—”

“Sam, I believe you.”

And one look at Gabriel’s face, and he knew he had meant it. Relief spread throughout Sam’s whole body, and he reached for Gabriel’s hand.

“I’m so sorry I didn’t tell you. All of it.”

“You’re forgiven, Sam. I get why you hesitated,” he said, brushing the back of his hand with his thumb.

“Thank you,” he said, relieved. “Gabriel? Can I ask you—what happened? I—I know you said you suspected about Bela, and I’m guessing you found out that we were working together…but obviously you didn’t know everything because then you wouldn’t have, um—”

“Ghosted?”

Sam bit his lips.

And then, Gabriel told Sam about Kip’s visit at the bakery, as well as the insinuations he had voiced. He also recounted his awkward encounter with Bela on the same night.

“I didn’t want to panic, but it wasn’t reassuring. And I have to admit, I—Sam, I—I don’t know how I can compete with someone you’ve been pining for so long.”

“You don’t have to. I’d never ask you this, but you don’t have to, Gabriel. I told you, I liked her, yes, but she's not the one I like now,” he squeezed his hand, stepping closer. "You are."

_And I certainly like you far more than I ever liked her._

Gabriel took a moment to reflect on it all, as he studied Sam’s face.

“So, what you’re saying is that…you went from turning me down in the hope of being with Bela—or because you had feelings for her at least—to turning her down because you had feelings for me.”

And then a smile appeared on Sam’s face.

“That’s the thing that I like the most about this,” he said, looking giddy. “Because it’s actually _not_ what happened.”

Gabriel squinted at him. “Um, you lost me. That’s exactly what happened.”

“Nope, it isn’t,” said Sam, beaming at him. “Technically, I didn’t turn you down, Gabriel. Not at first. Not on the night we met. I followed you home. Because I liked you. And I knew it on that morning. You said my face changed when Bela appeared, but…I don’t think it’s for the reason you think. That’s what I was getting at in my message. Knowing that she was your roommate only delayed what I already wanted. It made me hesitate. And the more I hesitated, the more it made me realize how much I wanted this. I’m telling you, if she hadn’t been your roommate, if she hadn’t shown up that morning when she did…I—she’s the reason I left. Not you. She confused me.”

And Gabriel, easing his hand on Sam’s neck, said, “And now?”

“No confusion.” And he tugged him towards him, and he breathed on his lips, “The opposite.”

And _finally_ , they ended the misunderstanding with a long, deep kiss. And just as they were beginning to become comfortable, the kettle began whistling.

“Wow, um, I totally forgot about that,” said Gabriel, catching his breath. “This is like the slowest kettle in the world.”

“Not slow enough,” nearly groaned Sam.

And they both chuckled. Sam took care of the coffees, while Gabriel examined more attentively what was on Sam’s coffee table in front of him.

“I can’t help but notice that this one here has my name on it,” he said, holding a bright yellow shoebox size present, with angels on it.

“It does,” said Sam, smiling. He handed Gabriel a mug. “I was carrying it earlier on my way to the bakery. And since I don’t have a tree…”

And then a massive grin spread across Gabriel’s face.

“What?” said Sam, taking a sip of his coffee.

“It’s funny you mention that.”

“What? A tree?”

“Yup. When you explained why you didn’t have decorations, I decided to get you one.” He put down his mug, fetched his green box with a bow on it.

A box far too small to hold a full-size tree.

Sam stared at Gabriel curiously.

“Um, is that box like Mary Poppins’ bag?”

And Gabriel smiled mischievously.

And not long after that, once Gabriel revealed to Sam that it was a projector, and that they had set it up together, a virtual gorgeous Christmas tree was displayed on Sam’s wall. It appeared real enough and kept changing tones and colors. Even the decorations, like the ornaments and lights, altered.

“There’s many ways you can set it up,” said Gabriel, looking at the instruction pamphlet. “I wasn’t sure which one you’d like but you can choose. It’s by the same company that did my fireplace at the bakery.”

“This is so cool,” said Sam, stunned. “If it wasn’t for the fact that it literally changes every ten seconds, I’d think it was real.”

“That’s the idea.”

And standing next to each other, Sam having an arm wrapped around Gabriel’s shoulders, and Gabriel resting his head against him, they admired the tree quietly.

“So? Good call?”

“Yes. Thank you,” he whispered and kissed his forehead.

“Not that I want to ruin this perfect moment…”

“But?” said Sam, amused.

“What did you get me?”

Sam burst into laughter. He grabbed the present in front of him and handed it to Gabriel.

“What is it?” he said, shaking the box delicately. “Is it fragile? What color is it?”

And then Sam’s smile widened. “Oh, you want to guess? Like a rematch?”

Gabriel, understanding what Sam was referring to, said, “Why not? Three clues. Three guesses.” And he shifted on his footing, almost preparing himself.

“Wait,” said Sam. “We haven’t even set the stakes yet.”

“Last time I chose them, and since I’m the one guessing this time around, you should be the one to decide.”

“All right.” Sam, staring at him, desperate to hold down his smirk. “If you win, you get to spend the night here. And,” he added, suddenly inspired, “I get the pleasure of cooking breakfast for you tomorrow morning.”

“Is that so? And if you win?” he whispered in his ear.

“You still spend the night here and _you_ get the pleasure of cooking breakfast for me.”

Gabriel’s smile widened. “You run a tough bargain.”

“Are those terms agreeable to you?”

Gabriel tilted his head, faking reflection.

“I have one tiny question. When you say cooking breakfast, is that like an euphemism or that’s really what you mean?” 

“I—both.”

“Somehow I feel like that answer was improvised.”

“And yet, you can’t prove it,” he said in a very serious tone, which was contradicted by his wide smile. “So, do you agree?”

“I do. What’s your first clue?”

“I was wearing a pair similar to those when we met.”

And Gabriel burst into laughter. “Correct me if I’m wrong, but I think you misunderstand how this works,” said Gabriel. “You’re supposed to make me guess, not blurt out the answer.”

“I understand perfectly. I didn’t say it. It was still a clue. And I just really want you to win.”

And he leaned in and kissed him assertively on the mouth.

“Wait, what about tomorrow?” said Gabriel, breaking the kiss. “I thought you said you were working.”

“Not all day. And you really wanna discuss this now?” And Sam embraced Gabriel, and once he was sure his grip was firm enough, in one swift move, he lifted Gabriel, who wrapped his legs around him.

“You make a fair point.” And after giving one more kiss, he said, “Bedroom. Now”

**Notes for the Chapter:**

> Hello everyone! Sorry for the delay. The last couple of days have been nuts. I will make sure that the last two chapters (ch24 &25) will be posted by tmr night! (Christmas)  
> I hope everyone (who is celebrating) is having a nice Christmas Eve!!  
> Thank you for reading!!
> 
> (Thank you Danica and Landrala! Merry Christmas!)


	24. Chapter Twenty-Four: Christmas Eve, Part Two

Just like his brother, though unbeknownst to him, Dean had had an overwhelming couple of days before Christmas.

On the twenty-third, his day at the garage had been long and slow, and sadly, his night at _The Milton’s_ had felt even longer and slower. Because it was the night before Christmas Eve, the store had been opened until ten o’clock, and it had been even more stressful to work at the booth as Castiel and Dean had to share their already cramped and awkward workspace with Garth and Alicia.

And despite the extra hands to help, work hadn’t slowed down for one second. No customer had been rude, _per se_ , but certain tones and looks (and huffing and puffing), and this in a not so subtle manner, had been disagreeable.

In addition to the taxing work, there was also the issue of Castiel and Dean’s tension to deal with. While anger had finally vanished, embarrassment, it seemed, had taken over the both of them.

Dean had thought long and hard on his conversation with Sam, and while Sam had urged him to simply start by showing him that he was ready to listen, it was far easier said than done.

Dean felt at a loss on how to approach the problem, fearing that too many things had been said.

And dreading to aggravate it even further.

And the pressure of saying something became heavier, especially considering that this was their last night at _The Milton’s._

_Tonight is my last chance. If I blow it, if I say something stupid—or say nothing at all—and let him leave, that’s it._

_No more prime time to share at the booth. No more excuses to run into him._

It was true that, unlike the previous year, Dean knew Castiel’s name (and address), so contacting him after the holidays wouldn’t be an impossible task.

And yet, due to his stubbornness, Dean knew deep down that if he didn’t handle the situation then, he certainly wouldn’t find the courage within him to do something about it _after_ the holidays.

And so, he passed the better part of the night glancing at Castiel, desperate to find the words—and the opportunity—to express himself.

Without success, regrettably.

Nothing but shy looks and mumblings between the two.

And then their shift ended, the store officially closed its doors, and all four of them were cleaning up the work stations in silence. With Castiel and Dean locking eyes. Both tired. Both debating on saying something. On what to say. But before either of them did, Alicia asked Castiel if he could help her fetch new wrapping rolls to replace them.

Not diverting his gaze from Dean, he agreed. And he waited a moment more, as if he was giving him the chance to speak.

But Dean remained silent.

So, Castiel followed Alicia quietly, and when she returned to the booth, it was without paper and without Castiel.

Castiel was gone.

Without saying goodbye.

Without saying anything at all.

Without Dean having had uttering one coherent word to him.

He had blown it.

And Dean felt his throat tighten.

As for the twenty-fourth, Dean's afternoon had been uneventful at _The Milton’s_. There had been a distinct frenzy in the air. A mixture of excitement and stress. But not more than that. People had been eager to run back home, employees like customers.

All except Dean.

Which was why, now that Dean had finished his shift—his very last one at _The Milton’s_ —he grabbed himself a pizza at the small bistro not far from the store, the one he passed every day on his way there from the garage, and headed to Bobby’s auto shop.

But instead of getting in his car and returning home, Dean stayed hidden at the garage.

In the lounge room, he put his sad pizza for one on the table for later, sighed deeply and dropped on one of the couches.

And slowly drifted into sleep.

And the sad pizza for one became a sad and _cold_ pizza for one.

Nearly past seven, however, he was briskly woken up by some commotion. For a second, Dean wondered it was someone trying to get in. Like a thief. Which made no sense. But then he realized what it was. ~~~~

Someone was _knocking_ on the front door.

Frowning, Dean left the couch with great effort and headed towards the entrance.

And his heart jumped once he spotted Castiel waiting at the door, all bundled up in his trench coat and red scarf, with a light layer of snow in his hair.

Thinking he must be hallucinating, Dean stared at him for an instant.

They exchanged a shy look and Dean unlocked the door to let him in. Castiel shook his coat and stomped hard on the carpet to get rid of the fluffy snow as Dean shut the door behind him.

And they stared awkwardly at each other.

“I—I can’t believe you’re here,” said Dean finally. “How did you know where I was? Or where I work?”

“I didn’t know you’d be here. But I had to start somewhere.” And noticing Dean’s confused expression, he added, “You said that the garage was walking distance from the store. I assumed it mustn’t have been too far. I Googled it.”

_Okay. I’ll give you that one. But—_

“There’s up to four garages in this neighborhood. How did you know it was this one?”

“Trial and error,” he confessed. “The first two places were a bust, but once I spotted the Impala in the parking lot here, I had a feeling this was the right place.”

_Of course._

Castiel glanced around the place, seemingly assessing if they were on their own, as the snow was quickly melting from his hair, sliding down the side of his face.

And his neck.

Dean swallowed. “Cas, it’s Christmas Eve,” he said. “What are you doing here?”

“I wanted to talk to you. It—it won’t take long. You might—I simply didn’t like how we left things.”

His heart racing, Dean then said, “Come on. Let’s go this way. It’s warmer and I’ll show you the place.”

Castiel nodded and reached for something next to him. It was at that moment that Dean noticed he had brought bags along with him.

“Here,” he said, picking one of them off the ground. “I’ll help you with that.”

“Thanks,” said Castiel. He followed Dean past the lobby, as he took off his damp scarf, and observed everything around him. Dean quickly showed him the rest of the garage, pointing at Bobby’s office, the lounge, the restroom facilities, and of course, the workshop.

“What were you working on?” asked Castiel.

“Um, I—honestly, I wasn’t really.” He put down Castiel’s bag on one of the empty chairs and offered Castiel a seat at the small table where his pizza box rested.

But neither of them sat down.

Castiel, still examining their surroundings, took off his coat and rested it on a chair.

He fixed his shirt quickly and faced Dean, who was standing still, with his arm crossed over his chest.

“So, I, um, I really didn’t want to disturb you. I’m not expecting anything here. I know things are messy and complicated, and I’m—but being Christmas Eve, I know you won’t need to come back to the store anymore. And given everything, I suppose you might have a good excuse to avoid it all together and—” he took a deep breath. “But I hope that won’t be the case. Dean, I—I wanted to thank you. For this month. Knowing that you were there made me look forward to going to work.”

While his voice was steady and clear, Castiel’s eyes, on the other hand, were slightly watery, and it made Dean’s heart beating so fast, he could feel it up to his ears.

Castiel shifted on his feet. “I’ll restrain from apologizing again because I fear I’ll simply embarrass myself. But, please, know that I really didn’t mean to deceive you. Or offend you. And if—”

“Cas, stop.”

Castiel lifted his eyes, worried.

Dean swallowed hard. “Sorry. I mean, stop, you don’t need to—I know you didn’t. And I—” Dean took a step forward. “I’m sorry I was mad when I found out. But I panicked. I felt like an idiot to have considered the idea that we—this whole situation hit me like a big cosmic joke. A reminder of where my place was. A punishment for having looked on the bright side for once.”

“But Dean—”

“And I’m super aware,” he continued, cutting him off, “that this says much more about me than it says about you.” He lowered his eyes a moment. “As you might have noticed, I have a thing about lying. And when—I just assumed the worse. That you were—because that’s been my general experience so far when it comes to lying. But I should have given you the benefit of the doubt. And as for why you didn’t tell me the truth right away, I get why you did it. I’m—I’m just sorry that you felt like you had to do that to feel comfortable, and I feel even worse that I apparently proved your point.”

He then felt Castiel’s hand reach gently for his. Dean cautiously glanced at Castiel, who was simply observing him patiently, listening to his every word.

“You didn’t prove my point, Dean,” he said, stepping closer still. “I knew the longer I waited before telling you, the more awkward it would be. But believe me, I was planning on telling you. And I can honestly say, I haven’t intended to do that in a really long time.”

Dean took a deep breath and felt the tension in his shoulders considerably lessen, and the pit in his stomach subdue. And after a long minute, during which the stares turned warmer and merrier, Dean said, “Cas, do you have to go anywhere? Are—you must be expected at your house—your parents’ house.”

Castiel shook his head, smiling. “I’m where I want to be. If you want the company.”

“You sure? I—it’s Christmas Eve. And I—besides a cold pizza, I don’t have much here.”

Castiel let out a laugh. “That sounds great. I think it will go very well with some of the food I brought along with me,” he said, pointing at his bags.

“You brought food?”

“Yeah. It was for you. No matter what happened. But my plan was to share it with you. You hungry?”

Dean nodded, suddenly gifted with a renewal of energy. To help him with the food, he grabbed the other bag that Castiel had carried, but stopped when he realized the bag was much heavier than he had conceived.

“Jeez. What’s in there?”

“Oh,” said Castiel, laughing. “Wait, that’s—that one isn’t food. That’s your present.”

Dean’s eyes widened, which made Castiel smirk. “Do you want to open it now?”

Highly curious, Dean nodded.

Castiel retrieved a big box from the bag and laid it on the table.

It did not take long for Dean to recognize the wrapping paper. And the style in which it had been wrapped.

“But this is—”

Castiel, beaming, said, “Open it.”

Dean gaped at him and, after eyeing the big box some more, he tore the paper off.

And just as he had expected, he found himself staring at the vintage record player. The one Castiel had wrapped right under his nose.

Still confused, he turned his eyes on Castiel.

“You’re giving me Gabriel’s present?”

“No, of course not,” he said, laughing wholeheartedly. “It was always yours, not Gabriel’s.”

“What?”

Castiel took a deep breath. “Okay, this is the last—little—lie. I swear. But this one was for your own good. I never meant to give this to Gabe. This was always meant to be yours. Open it and you’ll see.”

Stunned, Dean did as he was told. He opened the sealed box, and after carefully sliding the record player out of its box, he noticed a small engraving on the side: “For D. W.”

Dean was at a loss for words. His eyes kept bouncing from Castiel to the record player.

“But—but, no—” He stepped back, with his mouth opened. “That would mean that you bought this like…”

“It was for you, Dean,” he repeated. “I know how you love classic rock. And you kept talking about the cassette tapes you owned,” he said, laughing, “so I guessed you wouldn’t mind this relic.”

“But I can’t—Cas, this is—this is too much.”

Castiel frowned at him. “Too much? If you’re talking price, I don’t want to sound cheap, but I’ll let you know that I got this at a good deal. A friend of mine owns a record shop. I asked him about it and he called me back the same day. Now, tell me, do you have any records?”

“Nope,” said Dean, smiling and not even caring, as just the idea of owning a vintage record player was wonderful enough, and this, even without having any records to listen to.

“Now you do.” And he handed Dean a second present. And the moment he assessed Dean’s expression, Castiel added, “And before you tell me it’s too much, remember: my friend owns a record store.”

Dean pursed his lips for a second, but eventually a faint smile formed itself at the corner of his mouth. He then tore the paper once more, holding his breath. He turned to Castiel utterly shocked.

“Cas, I—how?”

“I told you. My friend—”

“But—but this is the original Led Zeppelin album. Like, _the_ album. With the Hindenburg disaster cover.” He examined the second one. “And _Fire of Unknown Origins_ by BOC? Those are my favourite bands.”

“I know. You told me.”

Feeling overwhelmed, Dean took a deep breath and observed more closely the third record, with his hands nearly shaking. But he didn’t recognize this one. The cover was simply black. With no inscription on it.

Dean shot a puzzled look at Castiel.

“Okay, so, I—I wasn’t sure if I should give you this,” said Castiel. “I hesitated. The record player and these two records were the initial gift.” He paused, staring at the third record, as if he was weighing on his words, and then said, “But the next thing I knew, I—I got inspired. And, well…”

“What is it?”

“Put it on and you’ll know.”

Eager and curious, he began setting up everything accordingly, and just as he was about to move the headshell, he stopped and asked Castiel, “It’s not Christmas music, right?”

Castiel laughed. “No. It’s not.”

“Okay, then.”

Dean had expected some obscure rock band. But he was pleasantly surprised to learn that this was not the case. Far from it.

A piano. No lyrics, simply instrumental. Not quite classical music though, as far as he knew.

The melody was pleasant. And familiar. Slow and yet not—

Dean blinked. He turned to Castiel with his mouth wide open.

“Is this—is that you playing?”

Castiel nodded.

Fascinated, Dean held his breath to listen more attentively.

_Sweet. Uplifting._

_With a hint of melancholy with the grave notes._

_It still sounds like him._

“How?” said Dean.

“I used to do that when I was in high school. Record myself, I mean. I had access to the necessary equipment to do it. Still do. I—I rarely play these days. But I felt like it. When I shopped for your gift, it was like stepping back into old habits. Music has always been important to me. It once was the most important part of my life. I—with time, I had to distance myself from it though. But after shopping for this, I—I sat down at a keyboard and—” Castiel gestured at the record playing.

“Wait, so you—this is—you made this? Like, not just recorded it, but this is your piece?”

Castiel nodded.

Touched at the gesture, Dean continued gaping at him, and spent the next few minutes listening carefully to every note, and feeling every movement and emotion, until the tune came to an end.

Silence then spread throughout the room, and Dean and Castiel remained still, gazing at each other.

Dean took a step forward and asked Castiel a question he had meant to ask since the Milton’s party.

“Cas, how are you not, like—” he swallowed hard, choking on his question.

“Playing more often?”

“Yeah. This is—I want to say really good, but that’s an understatement.”

Castiel lowered his eyes. “It’s a long story. And a bit of a downer.”

Dean felt a pang in his chest at Castiel’s last comment.

“I’d very much like to hear it,” he said gently. “If you’re okay with that.”

And after a moment of reflection, as though he was choosing his words correctly, Castiel said, “The short version, I suppose, is that I started playing at a very young age. And I loved it. And I was…rather good at it. Enough to have a real chance to get into very prestigious music schools. I managed to secure myself an audition for Julliard.” Dean opened his mouth, but bit hard on his lips, to let him finish, reminding himself of Castiel’s warning. “Around the same time though, I also often played with one of my friends’ band. I wasn’t _with_ the band,” he added, as he smiled at Dean’s expression, “I just sometimes played with them when I could. For fun. And it was. And then, nearly a week before my audition, I was approached by a manager, who offered me a spot with one of the groups he was overseeing. And I was tempted by that idea. Much more than I ever thought I would be. I explained the situation, and he gave me a few days to think about it, so I had to make a choice. Go with the band and miss my audition, or take a shot at getting into Julliard and miss my chance to travel and be part of a band. I knew which option would have killed my parents. The simple fact that I was contemplating the idea brought a massive amount of issues, even if I was eighteen and could make my own decisions. But I wanted to choose the option I wanted, not because someone was forcing me into it, nor because I was doing it out of spite.”

“And what did you do?” said Dean, intrigued.

“That’s the sad part. I never got to choose.” He took a deep breath and added, “Two days later, when I was still deciding, I got into an accident.”

Dean’s face fell.

“It was winter and it was slippery. A deer came out of nowhere, and this truck, coming from the opposite direction, swirled to avoid it and—” He let out a deep sigh. “Nobody died. Which is—I was very lucky. Especially when I consider what—” and he stopped talking, looking at Dean with grim expression.

“Considering what happened to my parents,” said Dean softly, finishing his sentence. And Castiel squeezed his hand.

“I’ll spare you the medical jargon,” said Castiel, continuing his tale, “but because of the debris and the way my car was hit, my right hand got smashed, and while my left hand remained intact, save a few cuts, my left shoulder got injured as well. Some tendons and ligaments were torn.”

Dean, completely confused, gently lifted Castiel’s right hand to have a better look at it. And sure enough, Dean discerned distinct scars on his hand and fingers.

“It healed, obviously,” said Castiel, understanding what Dean was looking for. “With surgery, physio and patience—a lot of patience—I got better. But given when the accident occurred, this was more than a step back. I was in no condition to play, so I missed both my audition and my spot in the band. And while I slowly managed to recover and use my hand for everyday tasks, playing piano—and playing like I used to—was impossible. The damage was too great. No matter how, there was no way for me to be academy material after that. And I tried. And as for playing in a band, while the standard _might_ have been a little more malleable, the injury in my shoulder made it difficult for me to play for a long period of time. Which was a problem, as you can imagine. So,” he said, sighing, and smiling faintly, “I tried to content myself with the fact that, at the very least, I could still play for myself, if I wanted to. But I have to admit that it crushed a part of my spirit. I’ve been a bit lost about what I was supposed to do after that, and when you’re confused about something like that, it tends to spread into other areas of your life.”

Dean took a moment to absorb the enormity of what Castiel had just told him. Glancing at Castiel’s right hand, which he was still holding, he lifted it right up to his chin, ready to kiss it.

“I’m so sorry this happened to you.”

“It’s okay. It happened a long time ago,” said Castiel, staring at him warmly. “I’m all right, now.”

Dean quickly kissed Castiel’s hand, and said, “And I’m really happy that you came out of this okay.”

Staring at each other intensely, they remained quiet, slowly easing closer to one another.

“Can I ask you something?”

“Of course.”

Smirking, Castiel slowly leaned in. “Can I seriously kiss you now?”

Their noses were touching. And Dean could feel Castiel’s breath on his lips.

“This is a place of work, you know?” said Dean teasingly.

“Yes, but I don’t work here.”

And without further ado, Castiel pressed his lips against his. And he had meant it. He had not slowly grown into the kiss, taking the time to lure Dean into it.

No. Running his fingers through Dean’s hair with one hand, and gripping Dean’s waist with the other, Castiel glued himself to him, and kissed him with confidence and tenderness.

The long, burning kiss they had been holding back for far too long.

Quite literally taking Dean’s breath away.

Rendering him weak in the knees.

And making him melt on the spot.

Soon enough, resting his forehead against Castiel’s, to catch their breaths, and unable to contain their grins, Dean said, “I got you a present too.”

“You did, huh?” said Castiel, chuckling as he remembered their shopping spree. “Can I try it on?”

“Yes. That's what I was hoping for. The only thing is that I don’t have it here. It’s at home.”

“Hmm. How wonderfully convenient.”

**Notes for the Chapter:**

> All right! Here it is!! Sorry again for the slight delay and the next (and final) chapter will be posted in a few hours!!  
> I hope everyone is having a wonderful day!!  
> Thank you for reading!
> 
> (and thank you to Danica and Landrala!)


	25. Chapter Twenty-Five: Christmas Morning

On Christmas morning, Dean found Castiel quietly watching fat snowflakes fall outside Dean’s kitchen window. The coffee machine was brewing, two mugs rested on the counter, and Castiel, his back turned to him, was dressed only with one of Dean’s flannel shirts and the bright blue boxers that Dean had given him the night before.

A sight that brought a smile to Dean’s face.

Without uttering a word, Dean stepped towards him and gently wrapped his arms around his torso, hugging him tightly.

“Aren’t you cold?” he whispered, kissing the back of his neck.

“That’s why I was making coffee.” He reached for Dean’s hand and leaned himself against him to feel his warmth. “You’re helping, though.”

Still holding him tightly, Dean buried his face in his shoulders, breathing in his scent, feeling blissful.

Castiel then turned to get a proper look at him. Smiling, he mimicked Dean, by easing his hands from his chest to his neck, and gave Dean a sweet kiss at the corner of his mouth.

“Morning.”

“Morning,” said Dean, grinning from ear to ear. “Why didn’t you wake me?”

“You looked so comfortable. I didn’t have the heart to wake you. When the coffee was ready, I was going to check up on you,” he said, pressing his mouth on Dean’s jawline, “but you beat me to it.”

Feeling tingles on the back of his neck, Dean shut his eyes and caressed Castiel’s back.

“Can I just say, you have the most amazing bed hair,” said Dean, biting on his lip as he eyed Castiel’s hair.

Castiel snorted. “Is that a fact?”

“Definitely. Did you sleep well?” asked Dean.

“Very much so, yes. You?”

“Best in ages.” And then, he added in a playful tone, “Once I got to go to sleep.”

Castiel, laughing, leaned his head backward to look at him. Lifting an eyebrow, he said, “I seem to recall that most of we did last night were your ideas. Including the, um, encore performance.”

“An idea, which was highly supported by you and, not to mention, most of what happened last night was still _your_ doing,” he said, laughing. “Imagine that.”

As they chuckled, Dean’s phone, which lay on the table, buzzed. Checking his phone, he noticed that it was late in the morning and that Sam had tried to call him a few times.

“Everything okay?” asked Castiel. The coffee finally ready, he poured them each a cup and handed one to Dean.

“I hope so. Sam called.” They sat cozily at the table. “Is it all right if I make a quick call? I wanna make sure he’s okay.”

“Of course,” said Castiel, blowing on his coffee. “I’d love to speak to him.”

Dean was about to dial, but paused when something suddenly occurred to him. “Um, I know we didn’t really talked about this,” he said, treading carefully, “but…do you know what happened between him and Gabriel? Do you think he’s with him?”

Castiel’s face lit up. “I certainly hope so.”

“We managed to patch things up,” said Dean, holding his hand. “Wanna find out if they did too?”

Castiel nodded vehemently. He suggested, however, that until they knew more about the Gabriel situation, Dean should perhaps begin his call privately with Sam. Slightly worried that his Christmas morning call might turn glum rather quickly, Dean nonetheless decided to be hopeful, and argued that no matter what, Sam would want to know that Castiel was with Dean, just as he wished Gabriel was with him.

Which was why he opted to use FaceTime.

Thankfully, their concerns had been unnecessary. Sam answered as he was in the middle of a fit of laughter, unable to say one word, despite his obvious attempt.

“Sam?” said Dean, chuckling at sound of his brother’s laugh. “You okay? What’s so funny?”

But Sam could not stop laughing, so much so, that he soon disappeared from the frame, still roaring with laughter.

And Gabriel appeared on the screen.

“Hey! Sorry, Sam seems to have lost the ability to speak. Might be my fault,” he said, not looking remotely sorry. “So, you’re Dean! Hello! Good to put a face to a name,” he said, waving. “And a voice,” he added, winking at him.

“Hey! Hi! Yes! You’re there!”

“Yup. Merry Christmas!” he said giddily, and Sam did too, as best he could.

“Merry Christmas,” said Dean as well. “Good to meet you too. And guess who’s here with me?”

On cue, Castiel slid his chair next to Dean, and making sure to appear within the frame, he waved at Gabriel on the screen.

“Hello, Gabriel. I’m so happy to see you.”

Gabriel leaned closer to the screen and squinted at them. “Cas? Is that you?”

“Yes, it’s—”

“Is that really you?” Gabriel asked again, but this time, in an overly dramatic manner. “It’s—it’s been so long! How can I be sure that the face I am gazing upon is really the one of my dearly beloved cousin?”

“Will you stop,” said Castiel, laughing wholeheartedly.

“Wait—cousins?”

“IS CASTIEL THERE TOO?” Sam yelled in the background. “I NEED TO SEE HIM.”

“Oh, guess who’s back,” said Gabriel, looking at something off screen.

“Wait! Cousins?” repeated Dean at the screen. He turned to Castiel, confused. “You didn’t tell me this!”

But before Castiel could say anything else, Sam appeared on the screen and yelled, “Oh my God, YES! Hi Castiel! I’m so happy to see you!”

“Hello, Sam! It’s nice to meet you too.”

“Sam,” said Dean, “did you know your boyfriend is a Milton too?”

“I—what?”

“Woah! My ears are bleeding. I am _not_ a Milton,” said Gabriel. And then he added, nodding his head, “Technically speaking.”

Both Sam and Dean looked at Castiel.

“He’s telling the truth,” he said to them. “His mother, my aunt, is a Milton. Which makes him one, but his last name was never Milton.”

“And I am very, very grateful. Now that this is settled, I need to—”

“But you’re still related,” said Sam. “I didn’t know that.”

“Yeah, me neither,” said Dean, lifting his eyebrow at Castiel. “You told me Gabe was your friend.”

“Telling you that would have made it incredibly easy for you to realize who I was,” argued Castiel. “And Gabriel can say whatever he wants, even if his last name isn’t Milton, his family ties is not something he usually advertises either.”

“That is correct.”

“Anything else I should know about the fam?” said Dean, amused.

Castiel shifted his eyes, thinking. “Um, no. Except that the chocolate from the _Chocolaterie_ is from Gabe’s bakery.”

“What?” said Sam and Dean at the same time, followed quickly by “Traitor!” from Gabriel. “You weren’t suppose to say!”

“But—why isn’t it advertised as such?” asked Dean. “That would be so good publicity for you.”

“Because that’s the deal I made with the family. I’m contributing, just as anonymously as possible.”

“As far as possible too,” said Castiel under his breath.

“I heard that.”

“Can I just say," said Sam, "I’m so happy to see everyone this morning." 

“Same.”

“Agreed. But—Sam, weren’t you supposed to go to work?”

“I did already. I went really early, did the few hours I was supposed to, and came back. I still have a lot to go through, but,” he said, making a face, “I’m not touching any of that until later tonight.”

“Good for you.”

“Thanks. And Dean?” asked Sam, tilting his head to the side. “I know this is totally off topic, but am I seeing this right? The boxes behind you. Are they the ones Benny left you to bring to his friend…like months ago?”

Dean groaned.

“It’s Christmas. Don’t make me feel bad, Sammy.”

“Who’s Benny?” asked Gabriel.

“My old roommate,” said Dean, sipping on his coffee. “He had to leave town for a family emergency a couple of months ago and I was supposed to bring his stuff to a friend of his, but…I…forgot.”

“Procrastinated,” said Sam.

“Whatever,” said Dean, rolling his eyes.

“Did you find another roommate?” asked Castiel, smirking.

“No, he didn’t!” said Sam eagerly.

“Roommate,” snorted Gabriel. “Yeah. Nice bed hair, Cas.”

And Dean, grinning, said to him, “I told you that hair is something." And adopting a softer tone, he said, "And to be clear, no, I didn’t find another roommate. Funny enough, that’s partially why I had to work at the store.”

And Castiel’s smile widened. “Interesting. I happen to know someone who’s been looking for a new place to live.”

“No more running?” asked Dean.

“Don’t really feel like it, no.”

“We’re gonna leave you two now,” said Sam.

“Because reasons,” added Gabriel. “On either accounts.”

“Very subtle, Gabe.”

“You know me.”

And laughing heavily, Sam said, “I’m very happy to have met you, Cas, and I can’t wait to see you in person.”

“Likewise, Sam. Gabe? I’d tell you to behave, but that never worked.”

And Gabriel winked at him with a mischievous grin on his face.

“Merry Christmas, Dean,” said Sam.

And with his heart full, feeling warm and giddy, Dean said, “Merry Christmas, Sam.”

**Notes for the Chapter:**

> And here it is! The last chapter! WOW. Thank you for reading! I honestly cannot believe I managed to do this. It was really touch and go near the end, I'm not gonna lie, but it's done!  
> I know I've said this already, but THANK YOU for reading. For those of you who got to follow the story throughout December, thank you so much for your support. It really meant a lot. And that's an understatement.  
> And for those of you who are just tuning in, thank you so much as well for sticking with this story until the end. I hope you enjoyed it! I had a lot of fun writing it :D  
> Posting every day was a new experience and I learned a lot. I'm really happy I did this, so thank you!!
> 
> Thank you to Danica and Landrala for all your help and support. Like really. Having you in my corner is incredible and I am very grateful. You are both saints to help me out. Thank you.
> 
> And I hope everyone is having a lovely holiday (no matter what it is!!).  
> Thank you :D

**Author's Note:**

> Thank you for reading!! I hope you enjoy this Christmas fluff!!  
> If everything goes well, I should be able to post a chapter a day *fingers crossed*
> 
> Thank you to [Danica_Dust](https://archiveofourown.org/users/Danica_Dust/pseuds/Danica_Dust/works) and Landrala who are always so incredibly helpful with notes and so supportive!!
> 
> Here's my [Tumblr](https://thefandomsinhalor.tumblr.com) if you feel like checking it out!  
> Have a nice day everyone! :D


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